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

HRID 2164789Notes

Reaction equation

HRID 2164789 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=1[C:15]([NH:17][CH2:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:16].C(=O)(O)[O-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=2[C:15]([NH:17][CH2:18][CH2:19][CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[O:16])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 27983352-amino-N-(3-imidazol-1-ylpropyl)benzamide

Product 1

HCID 27983362-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamideYield 45.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chlorobenzenesulphonyl chloride (1.56 g) was added in portions over 2 minutes to a solution of 2-amino-N-(3-imidazol-1-ylpropyl)benzamide (1.8 g) in water (50 ml) at 80° C. on a steam bath. The mixture was stirred at 80°-90° C. for 3 hours, cooled to room temperature and brought to pH 7 with saturated aqueous sodium bicarbonate solution. The crude product which had precipitated was extracted into dichloromethane (2×100 ml); the resulting solution was dried over magnesium sulphate and evaporated to give a solid. The solid was recrystallised from ethanol to give 2-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide (1.4 g), in the form of a white solid, m.p. 174°-176° C.

Workup

  1. customThe crude product which had precipitated
  2. extractionwas extracted into dichloromethane (2×100 ml)
  3. dry with materialthe resulting solution was dried over magnesium sulphate
  4. customevaporated
  5. customto give a solid
  6. customThe solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-6238ef570f9e42dd95371431c4a2d662
Source dataset
uspto-grants-1985_03
Patent number
US04507315

Reaction notes

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