Carbon Disulfide → HCID 19751554, compound

HRID 483806Notes

Reaction equation

HRID 483806 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:18])[CH2:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl/[CH:20]=[CH:21]\Cl.[C:23](=[S:25])=[S:24]>CS(C)=O.[OH-].[K+]>[S:24]1[CH:21]=[CH:20][S:25][C:23]1=[C:11]([C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)=[O:18])[C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[O:13]

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 643833cis-1,2-DichloroethyleneHCID 19751539HCID 19751539, compound

Product 1

HCID 19751554HCID 19751554, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14797Potassium HydroxideSolvent

Procedure

Isopropyl 3-(1,3-benzodioxol-5-yl)-3-oxopropionate (2.5 g) was dissolved in 30 ml of DMSO, to which 2.2 ml of 10N potassium hydroxide and 0.7 ml of carbon disulfide were added under ice cooling. The temperature of the resulting mixture was allowed to rise to room temperature, at which the mixture was stirred for 1 hour. The reaction mixture then turned to a reddish clear solution. After the reaction mixture was ice-cooled again, 1.066 g of cis-1,2-dichloroethylene were added, the temperature of the resultant mixture was allowed to rise to room temperature, followed by stirring for 3 hours. When the solution was poured into ice water, crystals precipitated. Those crude crystals were recrystallized from benzene-hexane, whereby 385 mg of isopropyl 2-(1,3-dithiol-2-ylidene)-3-[3,4-(methylenedioxy)phenyl]-3-oxopropionate were obtained as reddish crystals (yield: 11%).

Workup

  1. additionwere added under ice cooling
  2. customto rise to room temperature, at which
  3. temperaturecooled again
  4. customto rise to room temperature
  5. stirringby stirring for 3 hours
  6. customprecipitated
  7. customThose crude crystals were recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-d456b2558b184c77b5b6077fafc6aff5
Source dataset
uspto-grants-1993_07
Patent number
US05227398

Reaction notes

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