Carbon Disulfide → HCID 21245341, compound

HRID 620812Notes

Reaction equation

HRID 620812 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])(=[O:4])=[O: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:1][S:2]([CH2:5][C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])(=[O:3])=[O:4]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 65741,1,2-TrichloroethaneHCID 14797Potassium HydroxideHCID 21245336HCID 21245336, compound

Product 1

HCID 21245341HCID 21245341, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 18 g of isopropyl methylsulfonylacetate, 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, 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, 24.1 g of the title compound was obtained as pale yellow crystals. Upon recrystallization from isopropanol, they turned to white crystals. Melting point: 127°-127.5° 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-7ceede2aa8204b09b1f2a92cdccfc3b3
Source dataset
uspto-grants-1989_04
Patent number
US04822814

Reaction notes

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