Benzenesulfonyl chloride → N-[4-(1H-Imidazol-1-yl)butyl]benzenesulfonamide

HRID 64852Notes

Reaction equation

HRID 64852 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:15]=[CH:14][N:13]=[CH:12]1.C(=O)(O)[O-].[Na+]>ClCCl>[N:11]1([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 43794804-(1H-imidazol-1-yl)butan-1-amine

Product 1

HCID 13687303N-[4-(1H-Imidazol-1-yl)butyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure of Example 8 and reacting the appropriate benzenesulfonyl chloride with 1H-imdazol-1-propanamine or 1H-imidazol-1-butanamine in the presence of saturated sodium bicarbonate in dichloromethane for 16-48 hours, then crystallizing the respective products with ether and, if necessary, recrystallization from ethyl acetate or ethanol/dichloromethane gave the compounds of Examples 9-12 found in Table III below and gives the compounds of Examples 13-15 in Table III.

Workup

  1. customfor 16-48 hours
  2. customcrystallizing the respective products with ether
  3. customif necessary, recrystallization from ethyl acetate or ethanol/dichloromethane

Sources & evidence

ORD record
ord-7004de13ede5493f81982239cbef4afc
Source dataset
uspto-grants-1986_09
Patent number
US04610981

Reaction notes

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