Methylamine → N-Methyl-3-nitrobenzenesulfonamide

HRID 902717Notes

Reaction equation

HRID 902717 reaction equation
[CH3:1][NH2:2].[N+:3]([C:6]1[CH:7]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]>C1COCC1.O>[CH3:1][NH:2][S:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=1)(=[O:14])=[O:13]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 579071N-Methyl-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of MeNH2 (10 mL of a 2N solution in THF) and 10 mL of H2O was treated with a solution of 3-nitrobenzene sulfonyl chloride (884 mg, 4 mmole) in 4 mL of THF. The reaction was stirred for 2 hours, diluted with H2O and extracted with Et2O. The extracts were washed with H2O, 0.1N HCl, aqueous NaHCO3, dried, and the solvent removed, and gave the titled product, 608 mg (70%). MS (ESI) 217 (MH+).

Workup

  1. extractionextracted with Et2O
  2. washThe extracts were washed with H2O, 0.1N HCl, aqueous NaHCO3
  3. customdried
  4. customthe solvent removed

Sources & evidence

ORD record
ord-d46aa37074bb477e91ab1c6104e3f474
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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