Chloroacetyl chloride → 2-Chloro-N-(4-chlorobenzenesulfonyl)acetamide

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:12][CH2:13][C:14](Cl)=[O:15]>>[Cl:12][CH2:13][C:14]([NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])=[O:15]

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 6765032-Chloro-N-(4-chlorobenzenesulfonyl)acetamide

Procedure

The reactant N-chloroacetyl 4-chlorobenzene sulfonamide was prepared by mixing 30.0 g of 4-chlorobenzene sulfonamide and 60.0 ml of chloroacetylchloride. The mixture was refluxed for 6 hours, allowed to cool, and stand at room temperature overnight. The crystalline product was removed by filtration, washed repeatedly with hexane, and dried. The product consisted of 32.5 g of reactant (m.p. 122°-124° C.). Structure was confirmed by IR and NMR.

Workup

temperatureThe mixture was refluxed for 6 hours
temperatureto cool
customThe crystalline product was removed by filtration
washwashed repeatedly with hexane
customdried

Sources & evidence

ORD record: ord-9157d1aad09d476e98fe686e61eee7f5
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04347380

Reaction notes

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