supplementary material a facile synthesis of sulfonylureas ... · a facile synthesis of...

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Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2017

Supplementary material

A facile synthesis of Sulfonylureas via water assisted preparation of Carbamates

Dinesh Kumar Tanwar,a Anjali Ratan,a Manjinder Singh Gill*,a

aDepartment of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research (NIPER), S.A.S. Nagar, Punjab-160062, India

*E-mail: msingh@niper.ac.in

Table of Contents

Page

1H and 13C NMR spectrum of Phenyl butyl carbamate (1) S4

1H and 13C NMR spectrum of Phenyl methyl carbamate (2) S5

1H and 13C NMR spectrum of Phenyl ethyl carbamate (3) S6

1H and 13C NMR spectrum of Phenyl propyl carbamate (4) S7

1H and 13C NMR spectrum of Phenyl isopropyl carbamate (5) S8

1H and 13C NMR spectrum of Phenyl cyclopropyl carbamate (6) S9

1H and 13C NMR spectrum of Phenyl pentyl carbamate (7) S10

1H and 13C NMR spectrum of Phenyl hexyl carbamate (8) S11

1H and 13C NMR spectrum of Phenyl cyclohexyl carbamate (9) S12

1H and 13C NMR spectrum of Phenyl ((1r,4r)-4-methylcyclohexyl)carbamate (10) S13

1H and 13C NMR spectrum of Phenyl octyl carbamate (11) S14

1H and 13C NMR spectrum of Phenyl benzyl carbamate (12) S15

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2017

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1H and 13C NMR spectrum of Phenyl (1-phenylethyl) carbamate (13) S16

1H and 13C NMR spectrum of Phenyl phenethyl carbamate (14) S17

1H and 13C NMR spectrum of Phenyl dimethylcarbamate (15) S18

1H and 13C NMR spectrum of Phenyl diethylcarbamate (16) S19

1H and 13C NMR spectrum of Phenyl pyrrolidine-1-carboxylate (17) S20

1H and 13C NMR spectrum of Phenyl piperidine-1-carboxylate (18) S21

1H and 13C NMR spectrum of N-(butylcarbamoyl)-4-methylbenzenesulfonamide (19) S22

1H and 13C NMR spectrum of N-(methylcarbamoyl)benzenesulfonamide (20) S23

1H and 13C NMR spectrum of N-(ethylcarbamoyl)benzenesulfonamide (21) S24

1H and 13C NMR spectrum of N-(benzylcarbamoyl)benzenesulfonamide (22) S25

1H and 13C NMR spectrum of N-((1-phenylethyl)carbamoyl)benzenesulfonamide (23) S26

1H and 13C NMR spectrum of N-(ethylcarbamoyl)-4-methylbenzenesulfonamide (24) S27

1H and 13C NMR spectrum of 4-methyl-N-(propylcarbamoyl)benzenesulfonamide (25) S28

1H and 13C NMR spectrum of N-(isopropylcarbamoyl)-4-methylbenzenesulfonamide (26) S29

1H and 13C NMR spectrum of N-(hexylcarbamoyl)-4-methylbenzenesulfonamide (27) S30

1H and 13C NMR spectrum of N-(cyclohexylcarbamoyl)-4-methylbenzenesulfonamide (28) S31

1H and 13C NMR spectrum of N-(benzylcarbamoyl)-4-methylbenzenesulfonamide (29) S32

1H and 13C NMR spectrum of 4-methyl-N-((1-phenylethyl)carbamoyl)benzenesulfonamide (30) S33

1H and 13C NMR spectrum of 4-chloro-N-(methylcarbamoyl)benzenesulfonamide (31) S34

1H and 13C NMR spectrum of 4-chloro-N-(ethylcarbamoyl)benzenesulfonamide (32) S35

1H and 13C NMR spectrum of 4-chloro-N-(propylcarbamoyl)benzenesulfonamide (33) S36

1H and 13C NMR spectrum of 4-chloro-N-(isopropylcarbamoyl)benzenesulfonamide (34) S37

1H and 13C NMR spectrum of N-(benzylcarbamoyl)-4-chlorobenzenesulfonamide (35) S38

1H and 13C NMR spectrum of 4-bromo-N-(methylcarbamoyl)benzenesulfonamide (36) S39

1H and 13C NMR spectrum of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide (37) S40

1H and 13C NMR spectrum of 4-bromo-N-(cyclopropylcarbamoyl)benzenesulfonamide (38) S41

1H and 13C NMR spectrum of N-(benzylcarbamoyl)-4-bromobenzenesulfonamide (39) S42

1H and 13C NMR spectrum of 4-bromo-N-((1-phenylethyl)carbamoyl)benzenesulfonamide (40) S43

1H and 13C NMR spectrum of 4-bromo-N-(phenethylcarbamoyl)benzenesulfonamide (41) S44

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1H and 13C NMR spectrum of 4-methoxy-N-(methylcarbamoyl)benzenesulfonamide (42) S45

1H and 13C NMR spectrum of 4-methoxy-N-(((1r,4r)-4-methylcyclohexyl)carbamoyl) benzenesulfonamide (43) S46

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1H NMR spectra of Phenyl butyl carbamate (1)

13C NMR spectra of Phenyl butyl carbamate (1)

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1H NMR spectra of Phenyl methyl carbamate (2)

13C NMR spectra of Phenyl methyl carbamate (2)

S6

1H NMR spectra of Phenyl ethyl carbamate (3)

13C NMR spectra of Phenyl ethyl carbamate (3)

S7

1H NMR spectra of Phenyl propyl carbamate (4)

13C NMR spectra of Phenyl propyl carbamate (4)

S8

1H NMR spectra of Phenyl isopropyl carbamate (5)

13C NMR spectra of Phenyl isopropyl carbamate (5)

S9

1H NMR spectra of Phenyl cyclopropyl carbamate (6)

13C NMR spectra of Phenyl cyclopropyl carbamate (6)

S10

1H NMR spectra of Phenyl pentyl carbamate (7)

13C NMR spectra of Phenyl pentyl carbamate (7)

S11

1H NMR spectra of Phenyl hexyl carbamate (8)

13C NMR spectra of Phenyl hexyl carbamate (8)

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1H NMR spectra of Phenyl cyclohexyl carbamate (9)

13C NMR spectra of Phenyl cyclohexyl carbamate (9)

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1H NMR spectra of Phenyl ((1r,4r)-4-methylcyclohexyl)carbamate (10)

13C NMR spectra of Phenyl ((1r,4r)-4-methylcyclohexyl)carbamate (10)

S14

1H NMR spectra of Phenyl octyl carbamate (11)

13C NMR spectra of Phenyl octyl carbamate (11)

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1H NMR spectra of Phenyl benzyl carbamate (12)

13C NMR spectra of Phenyl benzyl carbamate (12)

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1H NMR spectra of Phenyl (1-phenylethyl) carbamate (13)

13C NMR spectra of Phenyl (1-phenylethyl) carbamate (13)

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1H NMR spectra of Phenyl phenethyl carbamate (14)

13C NMR spectra of Phenyl phenethyl carbamate (14)

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1H NMR spectra of Phenyl dimethylcarbamate (15)

13C NMR spectra of Phenyl dimethylcarbamate (15)

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1H NMR spectra of Phenyl diethylcarbamate (16)

13C NMR spectra of Phenyl diethylcarbamate (16)

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1H NMR spectra of Phenyl pyrrolidine-1-carboxylate (17)

13C NMR spectra of Phenyl pyrrolidine-1-carboxylate (17)

S21

1H NMR spectra of Phenyl piperidine-1-carboxylate (18)

13C NMR spectra of Phenyl piperidine-1-carboxylate (18)

S22

1H NMR spectra of N-(butylcarbamoyl)-4-methylbenzenesulfonamide (19)

13C NMR spectra of N-(butylcarbamoyl)-4-methylbenzenesulfonamide (19)

S23

1H NMR spectra of N-(methylcarbamoyl)benzenesulfonamide (20)

13C NMR spectra of N-(methylcarbamoyl)benzenesulfonamide (20)

S24

1H NMR spectra of N-(ethylcarbamoyl)benzenesulfonamide (21)

13C NMR spectra of N-(ethylcarbamoyl)benzenesulfonamide (21)

S25

1H NMR spectra of N-(benzylcarbamoyl)benzenesulfonamide (22)

13C NMR spectra of N-(benzylcarbamoyl)benzenesulfonamide (22)

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1H NMR spectra of N-((1-phenylethyl)carbamoyl)benzenesulfonamide (23)

13C NMR spectra of N-((1-phenylethyl)carbamoyl)benzenesulfonamide (23)

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1H NMR spectra of N-(ethylcarbamoyl)-4-methylbenzenesulfonamide (24)

13C NMR spectra of N-(ethylcarbamoyl)-4-methylbenzenesulfonamide (24)

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1H NMR spectra of 4-methyl-N-(propylcarbamoyl)benzenesulfonamide (25)

13C NMR spectra of 4-methyl-N-(propylcarbamoyl)benzenesulfonamide (25)

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1H NMR spectra of N-(isopropylcarbamoyl)-4-methylbenzenesulfonamide (26)

13C NMR spectra of N-(isopropylcarbamoyl)-4-methylbenzenesulfonamide (26)

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1H NMR spectra of N-(hexylcarbamoyl)-4-methylbenzenesulfonamide (27)

13C NMR spectra of N-(hexylcarbamoyl)-4-methylbenzenesulfonamide (27)

S31

1H NMR spectra of N-(cyclohexylcarbamoyl)-4-methylbenzenesulfonamide (28)

13C NMR spectra of N-(cyclohexylcarbamoyl)-4-methylbenzenesulfonamide (28)

S32

1H NMR spectra of N-(benzylcarbamoyl)-4-methylbenzenesulfonamide (29)

13C NMR spectra of N-(benzylcarbamoyl)-4-methylbenzenesulfonamide (29)

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1H NMR spectra of 4-methyl-N-((1-phenylethyl)carbamoyl)benzenesulfonamide (30)

13C NMR spectra of 4-methyl-N-((1-phenylethyl)carbamoyl)benzenesulfonamide (30)

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1H NMR spectra of 4-chloro-N-(methylcarbamoyl)benzenesulfonamide (31)

13C NMR spectra of 4-chloro-N-(methylcarbamoyl)benzenesulfonamide (31)

S35

1H NMR spectra of 4-chloro-N-(ethylcarbamoyl)benzenesulfonamide (32)

13C NMR spectra of 4-chloro-N-(ethylcarbamoyl)benzenesulfonamide (32)

S36

1H NMR spectra of 4-chloro-N-(propylcarbamoyl)benzenesulfonamide (33)

13C NMR spectra of 4-chloro-N-(propylcarbamoyl)benzenesulfonamide (33)

S37

1H NMR spectra of 4-chloro-N-(isopropylcarbamoyl)benzenesulfonamide (34)

13C NMR spectra of 4-chloro-N-(isopropylcarbamoyl)benzenesulfonamide (34)

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1H NMR spectra of N-(benzylcarbamoyl)-4-chlorobenzenesulfonamide (35)

13C NMR spectra of N-(benzylcarbamoyl)-4-chlorobenzenesulfonamide (35)

S39

1H NMR spectra of 4-bromo-N-(methylcarbamoyl)benzenesulfonamide (36)

13C NMR spectra of 4-bromo-N-(methylcarbamoyl)benzenesulfonamide (36)

S40

1H NMR spectra of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide (37)

13C NMR spectra of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide (37)

S41

1H NMR spectra of 4-bromo-N-(cyclopropylcarbamoyl)benzenesulfonamide (38)

13C NMR spectra of 4-bromo-N-(cyclopropylcarbamoyl)benzenesulfonamide (38)

S42

1H NMR spectra of N-(benzylcarbamoyl)-4-bromobenzenesulfonamide (39)

13C NMR spectra of N-(benzylcarbamoyl)-4-bromobenzenesulfonamide (39)

S43

1H NMR spectra of 4-bromo-N-((1-phenylethyl)carbamoyl)benzenesulfonamide (40)

13C NMR spectra of 4-bromo-N-((1-phenylethyl)carbamoyl)benzenesulfonamide (40)

S44

1H NMR spectra of 4-bromo-N-(phenethylcarbamoyl)benzenesulfonamide (41)

13C NMR spectra of 4-bromo-N-(phenethylcarbamoyl)benzenesulfonamide (41)

S45

1H NMR spectra of 4-methoxy-N-(methylcarbamoyl)benzenesulfonamide (42)

13C NMR spectra of 4-methoxy-N-(methylcarbamoyl)benzenesulfonamide (42)

S46

1H NMR spectra of 4-methoxy-N-(((1r,4r)-4-methylcyclohexyl)carbamoyl) benzenesulfonamide (43)

13C NMR spectra of 4-methoxy-N-(((1r,4r)-4-methylcyclohexyl)carbamoyl) benzenesulfonamide (43)