Water → N-Methyl-N-(2-nitrophenyl)methanesulfonamide

HRID 1249114Notes

Reaction equation

HRID 1249114 reaction equation
[CH3:1][NH:2][S:3]([CH3:6])(=[O:5])=[O:4].C[O-].[K+].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].O>CN(C)C=O>[CH3:1][N:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])[S:3]([CH3:6])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 738951-Fluoro-2-nitrobenzeneHCID 97632N-MethylmethanesulfonamideHCID 23664618Potassium methoxide

Product 1

HCID 13314625N-Methyl-N-(2-nitrophenyl)methanesulfonamideYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3.2 g of N-methyl methanesulfonamide in 50 ml of dry dimethylformamide is added 1.47 g of potassium methoxide. The mixture is stirred for 15 minutes. 2.8 g of 2-Fluoronitrobenzene is added and the mixture is heated to reflux for two hours. The dimethylformamide is removed on a rotary evaporator. The concentrated reaction mixture is poured into water. The crude product is extracted with CH2Cl2. The crude extracts are dried with MgSO4, filtered and concentrated on a rotary evaporator. The crude product is purified by recrystallization from butyl chloride-ethyl acetate. 3.4 g of product with m.p. 144°-145° C. is obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for two hours
  3. customThe dimethylformamide is removed on a rotary evaporator
  4. customThe concentrated reaction mixture
  5. extractionThe crude product is extracted with CH2Cl2
  6. dry with materialThe crude extracts are dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. customThe crude product is purified by recrystallization from butyl chloride-ethyl acetate

Sources & evidence

ORD record
ord-a4b446c5e57f478f8d86eb6a43e10be8
Source dataset
uspto-grants-1986_12
Patent number
US04629496

Reaction notes

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