Carbon Disulfide → Isopropyl (1,3-dithiol-2-ylidene)-(4-fluorophenyl)-acetate

HRID 620069Notes

Reaction equation

HRID 620069 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.[C:15](=[S:17])=[S:16].[OH-].[K+].Cl/[CH:21]=[CH:22]\Cl>CS(C)=O.O.CCCCCC>[S:16]1[CH:22]=[CH:21][S:17][C:15]1=[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 643833cis-1,2-DichloroethyleneHCID 23038995Isopropyl 4-fluorophenylacetate

Product 1

HCID 54389916Isopropyl (1,3-dithiol-2-ylidene)-(4-fluorophenyl)-acetate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of isopropyl 4 -fluorophenylacetate (98.1 g) in dimethylsulphoxide (1.2 l) there are added carbon disulphide (38.0 g) and then, slowly, a solution of potassium hydroxide (84.9 ) in water (150 ml). The mixture is stirred for 2 hours at 40° and cooled to room temperature. cis-1,2-Dichloroethylene (50 g) is added very slowly and the mixture is stirred at 45° for 2 hours. Water (1.5 l) and hexane (1 l) are added, the two phases are separated and the aqueous solution is extracted with hexane (3×1 l). The combined organic phases are washed with water (2×1 l), dried over magnesium sulphate and evaporated. The residue is crystallised from hexane. The product is dried in vacuo to constant weight to yield isopropyl (1,3-dithiol-2-ylidene)-(4-fluorophenyl)-acetate, m.p. 86°.

Workup

  1. stirringthe mixture is stirred at 45° for 2 hours
  2. customthe two phases are separated
  3. extractionthe aqueous solution is extracted with hexane (3×1 l)
  4. washThe combined organic phases are washed with water (2×1 l)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue is crystallised from hexane
  8. customThe product is dried in vacuo to constant weight

Sources & evidence

ORD record
ord-78fbf703d6bd453e99d93b5de3c9668a
Source dataset
uspto-grants-1989_04
Patent number
US04818765

Reaction notes

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