Hydrochloric Acid → 4-[(Dimethylsulfamoyl)amino]-N-phenylbenzamide

HRID 1982279Notes

Reaction equation

HRID 1982279 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:17][N:18]([CH3:23])[S:19](Cl)(=[O:21])=[O:20].Cl>N1C=CC=CC=1>[CH3:17][N:18]([CH3:23])[S:19]([NH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 699104-Amino-N-phenylbenzamideHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 133219734-[(Dimethylsulfamoyl)amino]-N-phenylbenzamideYield 57.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.0 g of 4-aminobenzanilide 4 dissolved in 10 ml of dried pyridine is added 1.01 g of dimethylaminosulfonyl chloride 5 at room temperature, and the mixture is stirred over-night. The reaction mixture is poured into ice-water, acidified with 6N hydrochloric acid, and extracted with a mixture of methylene chloride-methanol. The organic layer is extracted again with 10% sodium hydroxide solution. The alkaline layer is acidified with 6N hydrochloric acid; the precipitate is collected by filtration and recrystallized from methanol to give 864 mg of 4-[(dimethylaminosulfonyl)amino]benzanilide 6 as crystals, m.p. 213°-215° C.

Workup

  1. extractionextracted with a mixture of methylene chloride-methanol
  2. extractionThe organic layer is extracted again with 10% sodium hydroxide solution
  3. filtrationthe precipitate is collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-fe6216b011ca456882813f5f470d7872
Source dataset
uspto-grants-1986_06
Patent number
US04595780

Reaction notes

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