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

HRID 1959799Notes

Reaction equation

HRID 1959799 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-9dc742665884452eb55fdb09ff333aa8
Source dataset
uspto-grants-2013_04
Patent number
US08410272B2

Reaction notes

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