4-Chlorobenzenesulfonyl chloride → HCID 13280086, compound

HRID 2164787Notes

Reaction equation

HRID 2164787 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH3:15])=[O:5].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH3:15])=[O:5])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 204033292-Amino-N-[3-(2-methyl-1H-imidazol-1-yl)propyl]benzamide

Product 1

HCID 13280086HCID 13280086, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-N-[3-(2-methylimidazol-1-yl)propyl]benzamide (10.5 g) was dissolved in pyridine (50 ml) and 4-chlorobenzenesulphonyl chloride (12.35 g) was added in portions during five minutes. The temperature of the reaction mixture rose to 45° C. The solution was stirred at room temperature for 4 hours and the pyridine was evaporated in vacuo to give a brown oil. The oil was chromatographed on silica gel, eluting with a mixture of chloroform and methanol (19:1) to give 2-(4-chlorobenzenesulphonamido)-N-[3-(2-methylimidazol-1-yl)propyl]benzamide in the form of a white solid (7 g), m.p. 122°-123° C.

Workup

  1. customrose to 45° C
  2. customthe pyridine was evaporated in vacuo
  3. customto give a brown oil
  4. customThe oil was chromatographed on silica gel
  5. washeluting with a mixture of chloroform and methanol (19:1)

Sources & evidence

ORD record
ord-69d31def0e184a61b9b690ee9e0ac6d6
Source dataset
uspto-grants-1985_03
Patent number
US04507315

Reaction notes

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