Carbon Disulfide → HCID 86742946, compound

HRID 620813Notes

Reaction equation

HRID 620813 reaction equation
[CH2:1]([S:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])(=[O:6])=[O:5])[CH2:2][CH3:3].[C:12](=[S:14])=[S:13].[OH-].[K+].Cl[CH:18](Cl)[CH2:19]Cl>O.C(Cl)(Cl)Cl.CN(C)C=O>[S:13]1[CH:19]=[CH:18][S:14][C:12]1=[CH:3][CH2:2][CH2:1][S:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])(=[O:6])=[O:5]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 65741,1,2-TrichloroethaneHCID 14797Potassium HydroxideHCID 14931216HCID 14931216, compound

Product 1

HCID 86742946HCID 86742946, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 18.0 g of methyl n-propylsulfonylacetate, 7.6 g of carbon disulfide and 200 ml of dimethylformamide, 22.4 g of potassium hydroxide was added under ice-cooling. The resultant mixture was stirred for 2 hours. Thereafter, 13.3 g of 1,1,2-trichloroethane was added to the reaction mixture. followed by stirring at 80° C. for 3 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, 25.2 g of the title compound was obtained as pale yellow crystals. Upon recrystallization from methanol, they turned to white crystals. Melting point: 133°-135° C.

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-2a1b72d899f34b7c8fe75da7a3ab5e49
Source dataset
uspto-grants-1989_04
Patent number
US04822814

Reaction notes

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