N-methyl-2-pyrrolidone → HCID 18433361, compound

HRID 2305635Notes

Reaction equation

HRID 2305635 reaction equation
F[C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].CN1CCCC1=O.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][SH:30])=[CH:27][CH:26]=1.[H-].[Na+]>O>[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][S:30][C:2]2[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 10443188HCID 10443188, compound

Product 1

HCID 18433361HCID 18433361, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-fluoro4-nitrophenylacetate(1.05 g), N-methylpyrrolidinone(10 mL) and 4-methoxybenzyl mercaptan was stirred under argon and treated with sodium hydride(0.22 g of a 60% dispersion in mineral oil) and the resulting mixture was stirred at ambient temperature for 0.5 h. Water was added and the mixture was extracted with ether, and the extract was washed with brine, dried and evaporated to dryness. The residue was purified by flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product (1.35 g), [m/e365, (M+NH4)+].

Workup

  1. stirringwas stirred at ambient temperature for 0.5 h
  2. extractionthe mixture was extracted with ether
  3. washthe extract was washed with brine
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography
  7. washeluting
  8. temperaturewith increasingly polar mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-8c5b3bdeed1c41cbbedb3d947cd6a076
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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