Water → Benzenesulfonamide, 4-chloro-N-methoxy-3-nitro-

HRID 1356680Notes

Reaction equation

HRID 1356680 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17].O>N1C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:4][O:2][CH3:3])(=[O:14])=[O:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 18509259Benzenesulfonamide, 4-chloro-N-methoxy-3-nitro-Yield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride(0.90 g (10.8 mmol) was suspended in pyridine (3.0 ml). To this, under cooling with ice and with stirring, 4-chloro-3-nitrobenzenesulfonylchloride (2.56 g (10.8 mmol)) was added and the mixture was stirred under cooling with ice for one hour and at room temperature for 3 hours. Water (50.0 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with dilute hydrochloric acid and water successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2.02 g (76%) of 4-chloro-N-methoxy-3-nitrobenzenesulfonamide as pale yellow-white crystals.

Workup

  1. temperatureTo this, under cooling with ice
  2. stirringthe mixture was stirred
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with dilute hydrochloric acid and water successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a41d8b4830ee4341b537384905d23e2c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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