Dimethylformamide → 3-Acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine

HRID 1583538Notes

Reaction equation

HRID 1583538 reaction equation
CN(C)C=O.[H-].[Na+].[C:8]([OH:11])(=[S:10])[CH3:9].CS(O[CH:17]1[CH2:21][CH2:20][N:19]([C:22](=[N:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[O:26])[CH3:23])[CH2:18]1)(=O)=O>O>[C:8]([S:10][CH:17]1[CH2:21][CH2:20][N:19]([C:22](=[N:24][C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=2)=[O:26])[CH3:23])[CH2:18]1)(=[O:11])[CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 539971713-Methanesulphonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidineHCID 178418634HCID 178418634, compound

Product 1

HCID 540371453-Acetylthio-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidineYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 ml of anhydrous N,N-dimethylformamide were added 7.35 g of sodium hydride in the form of a 55% w/w/ dispersion in oil, followed by 12.5 g of thioacetic acid. The mixture was then stirred for 10 minutes, with ice-cooling, after which 40 g of 3-methanesulphonyloxy-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine were added. The mixture was then stirred for 3 hours at 65° C. After the reaction mixture had been allowed to cool, water was added and the mixture was extracted with ethyl acetate. The extract was washed with water and dried and then the solvent was distilled off under reduced pressure. The residue was purified by chromatography through a column of silica gel, eluted with a 2:1 by volume mixture of benzene and ethyl acetate, to give 30 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringThe mixture was then stirred for 3 hours at 65° C
  3. temperatureto cool
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by chromatography through a column of silica gel
  9. washeluted with a 2:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-64d9ed9ea2084fd89af5c58ee7587c48
Source dataset
uspto-grants-1985_11
Patent number
US04552873

Reaction notes

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