Methyl Isocyanate → N-(N-methylcarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one

HRID 1109288Notes

Reaction equation

HRID 1109288 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[C:5]([C:9]1[CH:10]=[C:11]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=1[OH:22])[CH:12]=[C:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18])([CH3:8])([CH3:7])[CH3:6]>>[CH3:1][NH:2][C:3]([N:15]1[CH2:16][CH2:17][C:13](=[CH:12][C:11]2[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]([OH:22])=[C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])[CH:10]=2)[C:14]1=[O:18])=[O:4]

Participants

3

Reactant 2

HCID 12228Methyl IsocyanateHCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

Product 1

HCID 54242406N-(N-methylcarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-oneYield 70.3%

Procedure

Methyl isocyanate (5.0 ml) was added to 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (277 mg, 0.75 mmole) (J. Med. Chem., p1995, 30, 1987) and the mixture was heated under reflux for 15 hours. The reaction mixture was evaporated under reduced pressure to obtain a residue, which was purified by using silica gel chromatography (n-hexane:ethyl acetate=4:1) and recrystallized from dichloromethane-ether, whereby 189 mg of the objective compound was obtained as white crystal in 70.3% yield. The physical constants are described on Table 1.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. customThe reaction mixture was evaporated under reduced pressure
  4. customto obtain a residue, which
  5. customwas purified
  6. customrecrystallized from dichloromethane-ether

Sources & evidence

ORD record
ord-8ae45c07cde249b98dcfac690981f14b
Source dataset
uspto-grants-1994_06
Patent number
US05319100

Reaction notes

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