1,4-Dimethylimidazole → N-(2-chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamide

HRID 1655889Notes

Reaction equation

HRID 1655889 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[N:4]=[CH:3]1.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16]>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][C:19]([C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([CH3:7])[N:4]=1)=[O:20])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 1387331,4-DimethylimidazoleHCID 174071Benzenesulfonyl isocyanate, 2-chloro-

Product 1

HCID 19789278N-(2-chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamideYield 37.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.0 g of 1,4-dimethylimidazole and 4.3 g of 2-chlorophenylsulfonyl isocyanate in 200 ml of toluene are refluxed for 6 h. The precipitate which forms on cooling is filtered off with suction and washed with acetone. The residue is suspended in acetonitrile/methanol and refluxed for 0.5 h. After cooling, the solid is filtered off with suction and dried under reduced pressure. 2.3 g of N-(2-chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamide with a melting point of 230°-231° C. are obtained. (Active ingredient Example No. 113).

Workup

  1. temperatureon cooling
  2. filtrationis filtered off with suction
  3. washwashed with acetone
  4. temperaturerefluxed for 0.5 h
  5. temperatureAfter cooling
  6. filtrationthe solid is filtered off with suction
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7250cc25762946cbb5c8a53d01ca6c84
Source dataset
uspto-grants-1993_10
Patent number
US05252540

Reaction notes

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