Ethanone, 1-(3,4-dichlorophenyl)- → 1-(3-Chloro-4-mercapto-phenyl)ethanone

HRID 1111525Notes

Reaction equation

HRID 1111525 reaction equation
[SH2:1].[Na].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][C:9](Cl)=[C:8]([Cl:13])[CH:7]=1)=[O:5]>CN1CCCC1=O>[Cl:13][C:8]1[CH:7]=[C:6]([C:4](=[O:5])[CH3:3])[CH:11]=[CH:10][C:9]=1[SH:1]

Participants

4

Reactant 2

HCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 86586439Sodium hydrogen sulphide

Product 1

HCID 143653711-(3-Chloro-4-mercapto-phenyl)ethanoneYield 90.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

110 g (1.48 mol) of sodium hydrogen sulphide (NaSH·H2O) are initially introduced together with 1 l of N-methylpyrrolidone and the water is removed at 160° C. with nitrogen. The mixture is cooled to 140° C. and 112 g (0.59 mol) of 3,4-dichloroacetophenone are added, and the mixture is reacted further at 160° C. for 3 hours, and N-methylpyrrolidone is distilled off. The residue is taken up in 1 l of water and filtered, and the filtrate is acidified at 0°-10° C. with half-concentrated hydrochloric acid. The precipitate is filtered off with suction, washed neutral and dried. Distillation under reduced pressure gives 99.8 g (90.7% of theory) of 2-chloro-4-acetylthiophenol of boiling point: 125°-130° C./0.1 mbar.

Workup

  1. customthe water is removed at 160° C. with nitrogen
  2. customthe mixture is reacted further at 160° C. for 3 hours
  3. distillationN-methylpyrrolidone is distilled off
  4. filtrationfiltered
  5. customis acidified at 0°-10° C. with half-concentrated hydrochloric acid
  6. filtrationThe precipitate is filtered off with suction
  7. washwashed neutral
  8. customdried
  9. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-3bc5b4db269b44bcb7c9007dba606a2a
Source dataset
uspto-grants-1990_12
Patent number
US04980510

Reaction notes

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