Ethanethiol → HCID 14576901, compound

HRID 1904620Notes

Reaction equation

HRID 1904620 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[C:12](=[O:22])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[C:12](=[O:22])[CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 14576852HCID 14576852, compound

Product 1

HCID 14576901HCID 14576901, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2.95 g of 6-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-piperidone, 3 ml of ethanethiol, and 50 ml of methylene chloride was added, under ice-cooling 5.06 g of anhydrous aluminum chloride. After stirring at room temperature for 1 hour, the mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with an aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, dried, and concentrated. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 2.75 g of 6-(4-chlorophenyl)-1-(4-hydroxyphenyl)-2-piperidone as colorless needles.

Workup

  1. additionwas added, under ice-
  2. additionthe mixture was poured into ice-cold water
  3. extractionextracted with chloroform
  4. washThe extract was washed with an aqueous sodium hydrogen carbonate solution
  5. dry with materiala saturated aqueous sodium chloride solution, dried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-ef6fc625ebc142b0ad20a74e7aed578b
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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