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

HRID 2164790Notes

Reaction equation

HRID 2164790 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](Cl)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:21]1([CH2:26][CH2:27][CH2:28][NH2:29])[CH:25]=[CH:24][N:23]=[CH:22]1.C(N(CC)CC)C.CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH:29][CH2:28][CH2:27][CH2:26][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[O:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 787361H-Imidazole-1-propanamineHCID 204033322-[(4-Chlorobenzene-1-sulfonyl)amino]benzoyl chloride

Product 1

HCID 27983362-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Chlorobenzenesulphonamido)benzoyl chloride (3.40 g) was added in portions to a stirred mixture of 3-imidazol-1-ylpropylamine (1.29 g), triethylamine (1.04 g) and dimethylformamide (25 ml) at room temperature. The temperature of the mixture rose to 33° C.; the mixture was then stirred at room temperature for 4 hours before pouring into water (500 ml). The aqueous solution was decanted from the crude product which had precipitated as a gum. This gummy material was dissolved in dichloromethane (50 ml), the solution was dried over magnesium sulphate and the solution was evaporated. The crude product was recrystallised from ethyl acetate to give 2-(4-chlorobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide, in the form of a white solid, m.p. 175°-177° C. (yield: 2.1 g).

Workup

  1. customrose to 33° C.
  2. customThe aqueous solution was decanted from the crude product which
  3. customhad precipitated as a gum
  4. dissolutionThis gummy material was dissolved in dichloromethane (50 ml)
  5. dry with materialthe solution was dried over magnesium sulphate
  6. customthe solution was evaporated
  7. customThe crude product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-84d477dfc8894d0cad76e8045b68b733
Source dataset
uspto-grants-1985_03
Patent number
US04507315

Reaction notes

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