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

HRID 2261638Notes

Reaction equation

HRID 2261638 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][NH2:16].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:16][CH3:15])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-

Product 1

HCID 67301Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-nitrobenzenesulfonyl chloride (2.0 g, 7.8 mmol) in THF (10 mL) was added excess methylamine (2M solution in THF). The reaction solution was stirred at room temperature for 1 hr. Water was then added and the product was extracted into chloroform. The combined extracts were washed, dried over sodium sulfate, filtered and evaporation to yield 2.3 g of the crude 4-chloro-N-methyl-3-nitrobenzenesulfonamide as an oil. The crude material was used in the subsequent step without further purification.

Workup

  1. extractionthe product was extracted into chloroform
  2. washThe combined extracts were washed
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporation

Sources & evidence

ORD record
ord-796faa74ece54d7996cd96292c01cdeb
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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