3-Nitrobenzamide → 1-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

HRID 1588032Notes

Reaction equation

HRID 1588032 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][S:16]([CH3:15])(=[O:18])=[O:17])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 125763-NitrobenzamideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chloride

Product 1

HCID 196035271-(Methylsulphonylaminocarbonyl)-3-nitrobenzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-nitrophenylcarboxamide (2 g) in 150 ml of dry tetrahydrofuran was cooled to 0° C. and treated with 609 mg of sodium hydride (60% oil dispersion). The reaction mixture was stirred for 20 minutes and then methanesulfonylchloride (1.18 ml) was introduced dropwise via syringe. After 5 minutes the reaction mixture became homogeneous and was warmed to room temperature and stirred overnight. The reaction mixture was diluted with 300 ml of ethyl acetate and was washed with brine. The organic extracts were dried, concentrated in vacuo, and the residue was chromatographed on silica gel (ethyl acetate then chloroform-methanol, 95:5 v/v) to yield 1.6 g of the title compound in pure form.

Workup

  1. waitAfter 5 minutes the reaction mixture became homogeneous
  2. stirringstirred overnight
  3. washwas washed with brine
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-17ff4023f4b14d038157070b4c950e28
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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