Dimethylamine → N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide

HRID 1891014Notes

Reaction equation

HRID 1891014 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][S:11](Cl)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:15][NH:16][CH3:17]>ClCCl>[CH3:15][N:16]([CH3:17])[S:11]([CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 13196775(3-Nitrophenyl)methanesulfonyl chloride

Product 1

HCID 28632733N,N-dimethyl-1-(3-nitrophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-Nitrophenyl)methanesulfonyl chloride (1.0 g, 0.0042 mol) in dry dichloromethane (25 mls) at room temperature dimethylamine (2M in THF, 5.3 ml, 0.105 mol) was added dropwise. The mixture was stirred for 3 hours then filtered through silica, then evaporated to give N,N-Dimethyl-C-(3-nitro-phenyl)-methanesulfonamide, 1.0 g, 1H NMR CDCl3 2.84 (6H, s, 2×CH3), 4.29 (2H, s, CH2), 7.60 (1H, m, ArH), 7.79 (1H, d, ArH), 8.25 (2H, m, ArH)

Workup

  1. filtrationthen filtered through silica
  2. customevaporated

Sources & evidence

ORD record
ord-af42523a1b354c079da19e443c7f03e8
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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