P-Toluenesulfonamide → HCID 54500394, compound

HRID 1164374Notes

Reaction equation

HRID 1164374 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[N:5][C:4](=[C:8](Cl)Cl)[N:3]=1.[Na].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[O:23]1CCOCC1>O>[CH3:22][C:12]1[CH:13]=[CH:14][C:15]([S:18]([NH:21][C:8]([C:4]2[NH:5][C:6]([Cl:7])=[C:2]([Cl:1])[N:3]=2)=[O:23])(=[O:19])=[O:20])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6269P-ToluenesulfonamideHCID 312751,4-DioxaneHCID 5360545SodiumHCID 124825724,5-Dichloro-2-(dichloromethylidene)-2H-imidazole

Product 1

HCID 54500394HCID 54500394, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 21.8 g (0.1 mol) of 4,5-dichloro-2-dichloromethylene-imidazole in 25 ml of dioxane was added to a suspension of 22 g (0.114 mol) of the sodium salt of p-toluenesulphonamide in 200 ml of water, while stirring. The mixture was then heated briefly to the boil and the product was filtered off while the mixture was still at the boiling point. The precipitate was dried and recrystallized from acetonitrile or toluene. In this way, 14 g (42% of theory) of N-(4-methylphenylsulphonyl)-4,5-dichloroimidazole-2-carboxylic acid amide with a melting point of 238° C. were obtained.

Workup

  1. temperatureThe mixture was then heated briefly to the boil
  2. filtrationthe product was filtered off while the mixture
  3. customThe precipitate was dried
  4. customrecrystallized from acetonitrile or toluene

Sources & evidence

ORD record
ord-4d53ecddf9ef41b8990da6920dab04bb
Source dataset
uspto-grants-1983_01
Patent number
US04369186

Reaction notes

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