Water → 4-(4-Chlorophenyl)-5-[4-(methylthio)phenyl]pentane-2,5-dione

HRID 432658Notes

Reaction equation

HRID 432658 reaction equation
[C-]#N.[Na+].[CH3:4][S:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23](=[O:25])[CH3:24])=[CH:17][CH:16]=1.O>CN(C)C=O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([C:10]([C:9]2[CH:12]=[CH:13][C:6]([S:5][CH3:4])=[CH:7][CH:8]=2)=[O:11])[CH2:22][C:23](=[O:25])[CH3:24])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 769854-(Methylthio)benzaldehydeHCID 981834-Chlorobenzalacetone

Product 1

HCID 187599824-(4-Chlorophenyl)-5-[4-(methylthio)phenyl]pentane-2,5-dioneYield 48.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
35 °C

Procedure

Sodium cyanide (90 mg, 1.87 mmol) was added to a solution of 4-(methylthio)benzaldehyde (300 mg, 1.97 mmol) in N,N-dimethylformamide (2 ml). While stirring the resulting mixture at 30-40° C., a solution of 4-(4-chlorophenyl)-3-buten-2-one (370 mg, 1.97 mmol) in N,N-dimethylformamide (3 ml) was dropped. The thus-obtained mixture was then stirred at the same temperature for 90 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed successively with water and brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off and the thus-obtained brown oil (762 mg) was separated and purified by preparative thin-layer chromatography on silica gel [developing solvent: hexane/diethyl ether (2/1)], whereby the title compound was obtained as a pale yellow oil (317 mg, 48.3%).

Workup

  1. stirringThe thus-obtained mixture was then stirred at the same temperature for 90 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe thus-obtained brown oil (762 mg) was separated
  7. custompurified by preparative thin-layer chromatography on silica gel [developing solvent: hexane/diethyl ether (2/1)], whereby the title compound

Sources & evidence

ORD record
ord-7b4b4d8d6ae84cfe83233c65d3df2e74
Source dataset
uspto-grants-2003_12
Patent number
US06664256B1

Reaction notes

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