transamidation Electronic Supplementary Information (ESI ... · 1 Electronic Supplementary...

1

Electronic Supplementary Information (ESI)

Sulphuric acid immobilized on silica gel (H2SO4-SiO2) as an eco-friendly catalyst for transamidation Sk. Rasheed,a,b D. Nageswar Rao, a,b A. Siva Reddy, a,b Ravi Shankar,b and Parthasarathi Das a,b,*

aAcademy of Scientific and Innovative Research (AcSIR); bMedicinal Chemistry Division, Indian Institute of Integrative Medicine(CSIR) Canal Road, Jammu-180001, J & K, India; E-mail: partha@iiim.ac.in

Table of contents

The1H and 13C NMR spectra of compounds Page 1-42

N-(p-Tolyl)benzamide(1a): H1 NMR & C13 NMR

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015

mailto:partha@iiim.ac.in

2

0102030405060708090100110120130140150160170f1 (ppm)

20.9

5

120.

29

127.

0212

8.78

129.

6113

1.77

134.

2713

5.08

135.

36

165.

70

Methyl 4-(3-methoxybenzamido)benzoate(1b): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

2.99

2.91

2.08

1.09

1.00

1.99

1.98

3.87

3.88

7.15

7.16

7.17

7.18

7.20

7.21

7.23

7.37

7.39

7.41

7.43

7.45

7.63

7.66

7.71

7.74

7.76

3

0102030405060708090100110120130140150160f1 (ppm)

55.4

655

.56

114.

3311

4.88

120.

4312

1.10

122.

6612

2.92

129.

5412

9.89

130.

02

159.

5815

9.85

162.

26

2,6-Dimethyl-N-phenylbenzamide(1c): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

6.12

3.12

3.16

0.94

0.96

1.18

1.00

2.28

3.88

7.09

7.10

7.12

7.13

7.14

7.15

7.38

7.40

7.45

7.49

4

0102030405060708090100110120130140150160170f1 (ppm)

18.4

9

55.5

0

112.

66

117.

9911

8.99

127.

4612

8.28

129.

7613

3.86

135.

6013

5.93

159.

95

165.

88

3-Methoxy-N-(pyrimidin-2-yl)benzamide(1d): H1 NMR & C13 NMR

5

N-(Cyclopropylmethyl)-3-methoxybenzamide(1e): H1 NMR & C13 NMR

6

0102030405060708090100110120130140150160170f1 (ppm)

3.51

10.7

2

44.9

9

55.4

6

112.

35

117.

5411

8.62

129.

54

136.

27

159.

81

167.

32

(3-Methoxyphenyl)(morpholino)methanone(1f): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

3.89

3.99

2.92

2.78

1.00

3.45

3.64

3.76

3.77

3.82

6.94

6.96

7.28

7.30

7.32

7.34

7

N-(Naphthalen-2-yl)-1-naphthamide(1g): H1 NMR & C13 NMR

8

0102030405060708090100110120130140150160170f1 (ppm)

116.

78

119.

7812

4.76

125.

1412

5.21

125.

2612

6.66

127.

4512

7.61

127.

7812

8.47

128.

9513

0.08

130.

8013

1.17

133.

7713

3.86

135.

42

167.

69

N-(Cyclopropylmethyl)-1-naphthamide(1h): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

2.10

2.06

1.12

2.05

0.98

1.12

2.09

1.06

2.11

1.00

0.29

0.30

0.31

0.33

0.55

0.56

0.58

0.60

1.07

1.08

1.09

1.11

1.12

1.13

1.14

3.39

3.41

3.43

6.12

7.44

7.46

7.48

7.50

7.52

7.54

7.56

7.57

7.61

7.62

7.86

7.90

7.92

8.30

8.32

9

0102030405060708090100110120130140150160170180f1 (ppm)

3.53

10.8

4

44.8

7

124.

7612

4.88

125.

4312

6.40

127.

0712

8.31

130.

1213

0.46

133.

6613

4.77

169.

54

Naphthalen-1-yl(piperidin-1-yl)methanone(1i): H1 NMR & C13 NMR

10

N-(Pyridin-2-yl)-1-naphthamide(1j): H1 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

1.02

1.10

2.12

2.06

1.02

1.05

1.06

0.98

1.02

1.00

6.85

6.86

6.88

7.40

7.48

7.66

7.69

7.70

7.81

7.88

7.90

8.31

8.33

8.40

8.41

9.35

11

N-(4-Bromopyridin-2-yl)-1-naphthamide(1k): H1 NMR & C13 NMR

12

N-(2-Chloropyridin-3-yl)-1-naphthamide(1l): H1 NMR & C13 NMR

13

N-(Pyrimidin-2-yl)-1-naphthamide(1m): H1 NMR & C13 NMR

-1.0-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

1.12

3.01

1.00

2.09

1.02

1.00

0.99

7.40

7.41

7.42

7.45

7.47

7.48

7.49

7.50

7.51

7.52

7.53

7.55

7.59

7.61

7.80

7.81

7.82

7.84

7.86

7.87

7.89

8.03

8.05

8.28

8.30

8.98

9.00

14

N-Phenylpivalamide(2a): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

9.01

1.00

2.02

1.98

1.32

7.08

7.10

7.12

7.30

7.32

7.34

7.52

7.54

7.07.17.27.37.47.57.67.77.8f1 (ppm)

1.00

2.02

1.98

7.08

7.10

7.12

7.30

7.32

7.34

7.52

7.54

0102030405060708090100110120130140150160170180190f1 (ppm)

27.6

6

39.6

2

119.

9612

4.22

128.

98

138.

01

176.

61

15

N-(p-Tolyl)pivalamide(2b): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

9.07

3.04

2.17

2.03

1.31

2.31

7.11

7.13

7.40

7.41

7.17.27.37.47.57.6f1 (ppm)

2.17

2.03

7.11

7.13

7.40

7.41

0102030405060708090100110120130140150160170180f1 (ppm)

20.8

3

27.6

6

39.5

2

120.

05

129.

4313

3.79

135.

47

176.

45

16

Methoxyphenyl)pivalamide(2c): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

9.08

2.94

1.91

1.00

1.93

1.30

3.79

6.84

6.86

7.27

7.41

7.43

0102030405060708090100110120130140150160170180f1 (ppm)

27.6

7

39.4

2

55.5

0

114.

05

121.

95

131.

12

156.

33

176.

53

17

N-(2,6-Dimethylphenyl)pivalamide(2d): H1 NMR & C13 NMR

0102030405060708090100110120130140150160170180f1 (ppm)

18.2

9

27.8

1

39.2

8

127.

1012

8.14

133.

9913

5.45

176.

56

18

Methyl 2-methoxy-4-pivalamidobenzoate(2e): H1 NMR & C13 NMR

19

N-(2-Iodophenyl)pivalamide(2f): H1 NMR & C13 NMR

0102030405060708090100110120130140150160170180190f1 (ppm)

27.7

2

40.1

8

90.1

0

121.

7012

5.71

129.

29

138.

2813

8.69

176.

82

20

N-(Pyridin-2-yl)pivalamide(2g): H1 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

9.05

1.04

1.07

1.00

2.07

1.33

7.02

7.03

7.04

7.05

7.68

7.70

7.72

8.04

8.24

8.26

7.07.58.0f1 (ppm)

1.04

1.07

1.00

2.07

7.02

7.03

7.04

7.05

7.68

7.70

7.72

8.04

8.24

8.26

N-(5-

Bromopyridin-2-yl)pivalamide(2h): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

8.99

1.04

0.92

0.99

1.00

1.31

7.79

7.81

8.17

8.18

8.20

8.29

21

N-(2-Chloropyridin-3-yl)pivalamide(2i): H1 NMR

22

N-(Thiazol-2-yl)pivalamide(2j): H1 NMR & C13 NMR

0102030405060708090100110120130140150160170180190f1 (ppm)

27.2

1

39.1

4

113.

72

137.

27

159.

08

176.

43

23

N-Phenylformamide(3a): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

3.09

0.96

4.06

2.06

0.98

1.03

1.04

1.00

7.09

7.11

7.16

7.18

7.19

7.29

7.31

7.32

7.34

7.36

7.54

7.56

8.18

8.33

8.67

8.70

8.96

0102030405060708090100110120130140150160f1 (ppm)

118.

8112

0.26

124.

8112

5.30

129.

0812

9.75

136.

8813

7.12

159.

99

163.

34

24

Methyl 4-formamidobenzoate(3b): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

6.07

1.98

2.03

4.08

1.00

1.04

3.91

7.15

7.17

7.64

7.66

8.00

8.03

8.05

8.44

8.85

25

Methyl 4-formamido-2-methoxybenzoate(3c): H1 NMR & C13 NMR

26

N-(2-Hydroxy-5-methylphenyl)formamide(3d): H1 NMR & C13 NMR

27

N-(2-Iodophenyl)formamide(3e): H1 NMR & C13 NMR

28

N-(Pyridin-3-yl)formamide(3f): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

1.00

0.96

2.38

1.15

7.36

7.48

7.50

8.24

8.26

8.47

8.71

29

N-(2-Chloropyridin-3-yl)formamide(3g): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

1.06

1.02

0.98

1.00

1.10

7.29

7.31

7.77

8.10

8.15

8.56

8.76

8.78

30

N-(5-Bromopyridin-2-yl)formamide(3h): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

1.00

0.90

1.11

1.12

2.01

1.09

1.05

0.98

0.83

6.81

6.83

7.77

7.79

7.83

7.85

8.17

8.19

8.36

8.51

8.87

9.28

9.31

9.47

0102030405060708090100110120130140150160170f1 (ppm)

111.

9111

5.19

116.

17

141.

1914

1.22

148.

5914

9.30

149.

5114

9.54

159.

25

162.

83

31

N-(Thiazol-2-yl)formamide(3i): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

1.11

1.05

1.00

7.05

7.06

7.47

7.48

8.63

32

N-Phenethylformamide(3j): H1 NMR & C13 NMR

0102030405060708090100110120130140150160170f1 (ppm)

35.4

737

.65

39.2

943

.31

126.

6112

6.87

128.

6712

8.78

128.

8212

8.91

137.

7213

8.62

161.

60

164.

83

33

Methyl 2-formamido-3-(1H-indol-3-yl)propanoate(3k): H1 NMR & C13 NMR

34

Piperidine-1-carbaldehyde(3l): H1 NMR

Morpholine-4-carbaldehyde(3m): H1 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

2.06

2.00

2.09

2.13

1.00

3.39

3.40

3.42

3.57

3.58

3.59

3.65

3.67

3.68

3.69

3.70

3.71

8.06

35

N- (p-Tolyl)acetamide(3n): H1 NMR

N-(4-Methoxyphenyl)acetamide(3o): H1 NMR

N-(4-

36

Fluorophenyl)acetamide(3p): H1 NMR & C13 NMR

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

3.74

2.47

2.31

1.00

2.16

6.97

6.99

7.02

7.43

7.44

7.45

7.46

7.50

37

N-(4-(Trifluoromethoxy)phenyl)acetamide(3q): H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

3.12

1.91

0.93

2.00

2.18

7.15

7.17

7.48

7.52

7.54

38

N-(4-Nitrophenyl)acetamide(3r): H1 NMR & C13 NMR

N-

39

(Pyridin-2-yl)acetamide(3s): H1 NMR

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

3.06

1.17

0.98

1.01

1.00

0.92

2.20

7.26

7.27

7.28

7.29

8.18

8.20

8.31

8.32

8.58

8.59

8.74

N-(4-Bromopyridin-2-yl)acetamide(3t): H1 NMR & C13 NMR

40

N-(Pyridin-3-yl)acetamide(3u): H1 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

3.20

1.02

1.03

2.00

1.00

2.21

7.03

7.04

7.05

7.06

7.72

7.74

8.23

8.25

8.26

8.27

8.28

9.36

41

N-(2-(Diethylamino)ethyl)-4-nitrobenzamide: H1 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

6.08

4.09

2.07

2.04

2.00

1.11

1.13

1.14

2.71

2.73

2.75

2.76

2.83

2.84

2.85

3.60

3.61

3.62

3.64

8.00

8.02

8.23

8.26

Procainamide: H1 NMR & C13 NMR

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

6.09

4.01

2.00

2.05

2.09

2.03

0.86

1.38

1.40

1.42

3.43

3.44

3.46

3.48

3.49

3.50

3.52

3.81

3.82

6.70

6.72

7.69

7.71

8.38

42

0102030405060708090100110120130140150160170180190200210220f1 (ppm)

9.53

37.5

8

49.1

9

56.0

0

114.

03

120.

76

130.

20

153.

60

171.

30

transamidation Electronic Supplementary Information (ESI ... · 1 Electronic Supplementary...

Documents

Supplementary Material (ESI) for Energy & Environmental ...authors.library.caltech.edu/19587/2/C0EE00014K.pdf · S1 provides scanning ... Supplementary Material (ESI) for Energy &

Electronic supplementary information (ESI) for Chemical

Electronic Supplementary Information (ESI) › suppdata › c9 › cc › c9cc05517g › c9cc05517g1.pdfElectronic Supplementary Information (ESI) Palladium-induced transformation

Electronic Supplementary Information (ESI) Section

coating on zinc Electronic Supplementary Information (ESI ... ·

Electronic Supplementary Information (ESI)

Electronic Supplementary Information (ESI) therapy and

Electronic Supplementary Information (ESI) advanced ... ·

Electronic Supplementary Information (ESI) Hierarchically … · 2013-07-01 · 1 † Electronic Supplementary Information (ESI) Hierarchically Inorganic–Organic Multi-Shelled Nanospheres

Electronic supplementary information (ESI) available ... · Electronic supplementary information (ESI) available ... Chinese Academy of ... (positive) Negative field electric increases

Electronic Supplementary information (ESI) Nanostructured ...Electronic Supplementary information (ESI) Nanostructured BN-TiO2 composite with ultra-high photocatalytic activity Bikramjeet

Electronic Supplementary Information (ESI) “Computational … · 2016-01-04 · 1 Electronic Supplementary Information (ESI) “Computational modeling reveals signaling subnetworks

Electronic Supplementary Material (ESI) optical and

electronic supplementary information ESI -revised

Electronic Supplementary Information (ESI) efficiency b ... ·

Electronic Supplementary Information (ESI) acetone sensing

Supplementary Material (ESI) for Molecular BioSystems This

Electronic Supplementary Information (ESI) polymer ... · Electronic Supplementary Information (ESI) Spectral properties of ionic benzotristhiazole based donor-acceptor NLO-phores

Electronic Supplementary Information (ESI) for Crystal

Electronic Supplementary Information (ESI) - The Royal … · · 2016-04-19Electronic Supplementary Information (ESI) * Correspondence Address Professor Ali Coskun Graduate School