Dimethylformamide → HCID 54490973, compound

HRID 1109360Notes

Reaction equation

HRID 1109360 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(=O)(OC1C=CC=C[C:29]=1[N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)N.CN(C=[O:45])C>>[O:37]1[CH2:38][CH2:39][N:34]([C:29]([N:11]2[CH2:12][CH2:13][C:9](=[CH:8][C:7]3[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=3)[C:10]2=[O:14])=[O:45])[CH2:35][CH2:36]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 19022130HCID 19022130, compoundHCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

Product 1

HCID 54490973HCID 54490973, compoundYield 90%

Procedure

To a solution of 3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (241 mg, 0.8 mmole) dissolved into DMF (2.4 ml), sodium hydride (60% in mineral oil, 96 mg, 2.4 mmole) was added under ice-cooling under nitrogen atmosphere with stirring for 30 min. Morpholinophenyl carbamate (249 mg, 1.2 mmole) was added thereto and the mixture was allowed to stand at room temperature for 4 hours. The reactant was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and evaporated. The obtained residue was recrystallized from dichloromethane/ether, whereby 300 mg of the objective compound (Ia-15) was obtained in 90% yield.

Workup

  1. additionwas added under ice-
  2. temperaturecooling under nitrogen atmosphere
  3. waitto stand at room temperature for 4 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe obtained residue was recrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-9bd98e5d2c36479aa38d2e28bd47b9e3
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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