Carbon Disulfide → 2-(1-Imidazolyl)-2-(4-isobutyl-1,3-dithiolan-2-ylidene)acetonitrile

HRID 649205Notes

Reaction equation

HRID 649205 reaction equation
[C:1]([CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)#[N:2].[C:9](=[S:11])=[S:10].[OH-].[K+].Br[CH2:15][CH:16](Br)[CH2:17][CH:18]([CH3:20])[CH3:19]>O.CS(C)=O>[N:4]1([C:3](=[C:9]2[S:11][CH:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:15][S:10]2)[C:1]#[N:2])[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 11804695(1-Imidazolyl)acetonitrileHCID 136059371,2-Dibromo-4-methylpentane

Product 1

HCID 538430812-(1-Imidazolyl)-2-(4-isobutyl-1,3-dithiolan-2-ylidene)acetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixed solution of 0.55 g (0.005 mole) of 1-cyanomethylimidazole, 0.4 g (0.005 mole) of carbon disulfide and 10 ml of dimethyl sulfoxide was added 0.8 g (0.014 mole) of potassium hydroxide powder with stirring, and the reaction was carried out at room temperature for 1 hour. Then, 1.5 g (0.006 mole) of 1,2-dibromo-4-methylpentane was added dropwise with stirring, and the resulting solution was subjected to reaction for 2 hours. After completion of the reaction, 20 ml of water was added to the reaction solution, after which the resulting mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with water and dried. The solvent was distilled off and the residue was purified by silica gel chromatography to obtain 0.45 g of the Z isomer and 0.3 g of the E isomer individually in the form of colorless crystals.

Workup

  1. stirringwith stirring
  2. customthe resulting solution was subjected to reaction for 2 hours
  3. additionwas added to the reaction solution
  4. extractionafter which the resulting mixture was subjected to extraction with ethyl acetate
  5. washthe organic layer was washed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe residue was purified by silica gel chromatography
  9. customto obtain 0.45 g of the Z isomer and 0.3 g of the E isomer individually in the form of colorless crystals

Sources & evidence

ORD record
ord-c41aa2c9f7ca40069df0fca2f6979975
Source dataset
uspto-grants-1988_04
Patent number
US04738976

Reaction notes

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