Ammonia → 2-Chloro-5-nitrobenzenesulfonamide

HRID 1979603Notes

Reaction equation

HRID 1979603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[NH3:15]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:15])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 206302-Chloro-5-nitrobenzenesulfonyl chloride

Product 1

HCID 667842-Chloro-5-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-5-nitrobenzenesulphonyl chloride (5.12 g, 20 mmole) was added in portions to liquid ammonia with stirring at -78° C. (methanol/dry-cold). The mixture was stirred for 0.5 h. and the excess ammonia then allowed to evaporate. The residue was crystallised from aqueous ethanol (1:1) to afford lustrous prisms of 2-chloro-5-nitrobenzenesulphonamide, 4.42 g, 93%, (m.p. 180°-187° C.). TLC analysis (CH2Cl2) showed one spot (Rf =0.2). Spectroscopic data was consistent with the product.

Workup

  1. customto evaporate
  2. customThe residue was crystallised from aqueous ethanol (1:1)

Sources & evidence

ORD record
ord-f3b05ba495164c2dbfedc099793ad14e
Source dataset
uspto-grants-1984_11
Patent number
US04481268

Reaction notes

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