p-Chlorothiophenol → 3'-(4-Chlorophenylthio)-4'-nitroacetophenone

HRID 1087185Notes

Reaction equation

HRID 1087185 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=2[N+:8]([O-:10])=[O:9])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7815p-ChlorothiophenolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 104427551-(3-Chloro-4-nitrophenyl)ethanone

Product 1

HCID 103805263'-(4-Chlorophenylthio)-4'-nitroacetophenoneYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3'-chloro-4'-nitroacetophenone (1.5 g), 4-chlorothiophenol (1.63 g) and potassium carbonate (1.56 g) in toluene (15 ml) was stirred at 70° C. for 5 hours. Ethyl acetate and water were added, and the organic layer was separated, washed with water, dried and evaporated to dryness. The residue was washed with toluene to give yellow crystals of 3'-(4-chlorophenylthio)-4'-nitroacetophenone (1.9 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. customdried
  4. customevaporated to dryness
  5. washThe residue was washed with toluene

Sources & evidence

ORD record
ord-498c9783497a48b38347c9b20a02403c
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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