Methylamine → N-methyl-2-nitrobenzene-1-sulfonamide

HRID 1487225Notes

Reaction equation

HRID 1487225 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].CN.[CH2:16]([N:18](CC)CC)C>ClCCl.O>[CH3:16][NH:18][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chloride

Product 1

HCID 264906N-methyl-2-nitrobenzene-1-sulfonamideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitrobenzene-1-sulfonyl chloride (30 g, 0.14 mol) in dichloromethane (500 mL) was slowly added a solution of methylamine in water (30%, 15.3 g) and triethylamine (38 mL, 0.27 mol) respectively. The mixture was stirred at room temperature for 1 hour and then evaporated. The residue was subjected to silica gel chromatography to afford the product N-methyl-2-nitrobenzenesulfonamide (26 g, yield 90%).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-8b57428bfabc44f6b42ec49310d00967
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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