Carbon Disulfide → HCID 21245351, compound

HRID 620811Notes

Reaction equation

HRID 620811 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3].[C:10](=[S:12])=[S:11].[OH-].[K+].Cl/[CH:16]=[CH:17]\Cl>O.C(Cl)(Cl)Cl.CN(C)C=O>[S:11]1[CH:17]=[CH:16][S:12][C:10]1=[CH:1][S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 643833cis-1,2-DichloroethyleneHCID 2759918Methanesulfonylacetic acid methyl ester

Product 1

HCID 21245351HCID 21245351, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 15.2 g of methyl methylsulfonylacetate, 7.6 g of carbon disulfide and 200 ml of dimethylformamide, 14.0 g of potassium hydroxide was added under ice-cooling. The resultant mixture was stirred for 3 hours. Thereafter, 9.7 g of cis-1,2-dichloroethylene was added, followed by stirring at 80° C. for 4 hours. After cooling the reaction mixture, chloroform and water were added and the resulting organic layer was separated. Upon removal of the solvent by distillation under reduced pressure, 20.9 g of the title compound was obtained as pale yellow crystals. Upon recrystallization from a mixed solvent of chloroform and n-hexane, they turned to white crystals. Melting point: 166°-168° C. (decomposed).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionwere added
  4. customthe resulting organic layer was separated
  5. customUpon removal of the solvent
  6. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-31daf46e689444fab9094eaf7c6d49e2
Source dataset
uspto-grants-1989_04
Patent number
US04822814

Reaction notes

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