Acetyl chloride → HCID 22460335, compound

HRID 1937280Notes

Reaction equation

HRID 1937280 reaction equation
[CH:1]1([S:7][CH2:8][S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:23](Cl)(=[O:25])[CH3:24]>CC(C)=O>[CH:1]1([S:7][CH2:8][S:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:23](=[O:25])[CH3:24])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 13006799HCID 13006799, compound

Product 1

HCID 22460335HCID 22460335, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

In 300 g of acetone was dissolved 26 g of the cyclohexylthio(4-hydroxyphenylthio)methane crude product in Synthesis Example 10. To this were added 21 g (0.15 mol) of potassium carbonate and 8.7 g (0.11 mol) of acetyl chloride. While heating in an oil bath at 70° C., the solution was ripened for 4 hours. At the end of ripening, the inorganic salt was filtered and washed with 50 g of acetone. The filtrate and wash liquid combined was concentrated, and the residue was dissolved in 300 g of dichloromethane and washed with 50 g of water. The organic layer was concentrated in vacuum again, obtaining 30 g of an oily product, which was used in the subsequent reaction without further purification.

Workup

  1. customin Synthesis Example 10
  2. filtrationthe inorganic salt was filtered
  3. washwashed with 50 g of acetone
  4. washThe filtrate and wash liquid
  5. concentrationcombined was concentrated
  6. dissolutionthe residue was dissolved in 300 g of dichloromethane
  7. washwashed with 50 g of water
  8. concentrationThe organic layer was concentrated in vacuum again

Sources & evidence

ORD record
ord-83648641293b45b69ebeae2eec4df068
Source dataset
uspto-grants-2002_05
Patent number
US06395446B1

Reaction notes

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