Benzenesulfonyl chloride, 4-chloro-3-nitro- → Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-

HRID 536046

Reaction equation

HRID 536046 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].Cl.[CH3:16][NH2:17]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:17][CH3:16])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 6364545Methylamine hydrochloride

Product 1

HCID 67301Benzenesulfonamide, 4-chloro-N-methyl-3-nitro-Yield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-3-nitrobenzenesulfonyl chloride (10 g, 39.1 mmol) in THF (100 mL) was cooled to −40° C. before being treated with a solution of methylamine hydrochloride (2.64 g, 39.1 mmol) in 10 ml of water followed by TEA (5.44 mL, 39.1 mmol). The reaction mixture was stirred and allowed to warm to room temperature over 1 hour before being partitioned between 350 mL EtOAc and 30 mL brine. The organic layer was washed twice with brine, dried over MgSO4 and subjected to flash chromatography (330 g silica gel, 0-40% EtOAc/hexane) to afford 4-chloro-N-methyl-3-nitrobenzenesulfonamide (6.38 g, 65%) as a light yellow solid. MS (m/z) 251.0 (M+H+).

Workup

  1. custombefore being partitioned between 350 mL EtOAc and 30 mL brine
  2. washThe organic layer was washed twice with brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-0f87bf007f8d43d0813b84f4291b22b7
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Linked notes

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