Water → 2-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide

HRID 2164785Notes

Reaction equation

HRID 2164785 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[O:5].O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=2[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[O:5])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 27983352-amino-N-(3-imidazol-1-ylpropyl)benzamide

Product 1

HCID 27983362-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamideYield 43.3%

Procedure

2-Amino-N-(3-imidazol-1-ylpropyl)benzamide (32.9 g) was dissolved in pyradine (165 ml) and 4-chlorobenzenesulphonyl chloride (41.2 g) was added in portions. The temperature of the reaction mixture rose to 52° C. The solution was stirred at room temperature for 4 hours and poured into water (1.5 l) to precipitate an oil which slowly solidified on standing. The solid was collected, washed with water and recrystallised from ethanol to give 2-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)-benzamide (24.4 g), in the form of a white solid, m.p. 175°-177° C.

Workup

  1. additionwas added in portions
  2. customrose to 52° C
  3. customto precipitate an oil which
  4. customThe solid was collected
  5. washwashed with water
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-96fecb8c48b74b7f9c9f97fe3766f328
Source dataset
uspto-grants-1985_03
Patent number
US04507315

Reaction notes

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