Ethanol → 2-(1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-oxo-3-m-tolyl-propionitrile

HRID 1828192Notes

Reaction equation

HRID 1828192 reaction equation
[Na].[CH:2]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([CH2:15][C:16]#[N:17])=[CH:14][C:9]=3[N:8]([CH3:18])[C:7]2=[O:19])[CH2:5][CH2:4][CH2:3]1.[CH2:20]([OH:22])[CH3:21]>>[CH:2]1([N:6]2[C:10]3[CH:11]=[CH:12][C:13]([CH:15]([C:20](=[O:22])[C:21]4[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][CH:10]=4)[C:16]#[N:17])=[CH:14][C:9]=3[N:8]([CH3:18])[C:7]2=[O:19])[CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 22063940HCID 22063940, compound

Product 1

HCID 220639752-(1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-oxo-3-m-tolyl-propionitrile

Conditions

Temperature
75 °C

Procedure

Sodium metal (1.2 g) was diluted with ethanol (12 mL). After dissolution (1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-acetonitrile (2.0 g, 8.29 mmol) was added followed by ethyl 3-methyl benzoate (2.0 mL). The reaction was heated to 75° C. for 2.5 hours then cooled and extracted into ethyl acetate from saturated sodium bicarbonate. Chromatography on silica gel gave the desired 2-(1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-3-oxo-3-m-tolyl-propionitrile.

Workup

  1. additionwas added
  2. temperaturethen cooled
  3. extractionextracted into ethyl acetate from saturated sodium bicarbonate

Sources & evidence

ORD record
ord-47251fd9fd784179aed1f70cf7a541dd
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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