3-Nitrobenzamide → 3-Nitro-N-(2-propylsulfonyl)phenylcarboxamide

HRID 1588034Notes

Reaction equation

HRID 1588034 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][CH:16]([S:18](Cl)(=[O:20])=[O:19])[CH3:17]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][S:18]([CH:16]([CH3:17])[CH3:15])(=[O:20])=[O:19])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 125763-NitrobenzamideHCID 24758Sodium hydrideHCID 824082-Propanesulfonyl chloride

Product 1

HCID 233531523-Nitro-N-(2-propylsulfonyl)phenylcarboxamide

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 530 mg of sodium hydride (60% oil dispersion). The reaction mixture was stirred for 20 minutes and then 2-propylsulfonylchloride (1.5 ml) was introduced dropwise via syringe. After 5 minutes the reaction mixture became homogeneous and was warmed to room temperature and stirred for 2 hours. 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 (chloroform-methanol, 95:5 v/v) to yield 0.6 g of the title compound in pure form.

Workup

  1. waitAfter 5 minutes the reaction mixture became homogeneous
  2. stirringstirred for 2 hours
  3. washwas washed with brine
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel (chloroform-methanol, 95:5 v/v)

Sources & evidence

ORD record
ord-cca3d61eab7d453897fb494f6017fc31
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

Loading…