Dichloromethane → N-(4-{[3-(1H-imidazol-1-yl)propyl]sulfamoyl}phenyl)acetamide

HRID 64854

Reaction equation

HRID 64854 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:10]([NH:13][C:14]1[CH:23]=[CH:22][C:17]([S:18](Cl)(=[O:20])=[O:19])=[CH:16][CH:15]=1)(=[O:12])[CH3:11].[OH-].[Na+].ClCCl>O>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][S:18]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][C:10](=[O:12])[CH3:11])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8481N-Acetylsulfanilyl chlorideHCID 14798Sodium HydroxideHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 3397673N-(4-{[3-(1H-imidazol-1-yl)propyl]sulfamoyl}phenyl)acetamideYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.25 g of 1H-imidazol-1-propanamine in 25 ml of water was stirred at room temperature then 2.34 g of N-acetylsulfanilyl chloride was added and stirring was continued for 20 hours resulting in a clear solution. With the addition of 4 ml of 5N sodium hydroxide the solution turned milky and resulted in the separation of an oil. The addition of dichloromethane resulted in the formation of a suspended precipitate which was collected by filtration and gave 2.67 g of the desired compound as tan crystals, mp 178°-180° C.

Workup

  1. stirringstirring
  2. customresulting in a clear solution
  3. customresulted in the separation of an oil
  4. customresulted in the formation of a suspended precipitate which
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7d37fe7c315a4b5f83ebf1ad3974096d
Source dataset
uspto-grants-1986_09
Patent number
US04610981

Linked notes

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