Benzyl Chloride → HCID 2748891, compound

HRID 1719612Notes

Reaction equation

HRID 1719612 reaction equation
ClC(Cl)=C[N:4]=[N:5][S:6]([C:9]1[CH:14]=CC(C)=CC=1)(=O)=O.[S-2:17].[Na+].[Na+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C.O>[CH2:20]([S:17][C:9]1[S:6][N:5]=[N:4][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 14804Sodium SulfideHCID 13553897HCID 13553897, compound

Product 1

HCID 2748891HCID 2748891, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

An ethanol (0.5 ml) solution of 1,1-dichloro-2-(p-toluenesulfonylazo)ethene (280 mg, 1.00 mmol) was slowly added to a water (1.0 ml)-ethanol (0.5 ml) solution of 600 mg (2.50 mmol) of sodium sulfide (Na2S.9H2O) under ice cooling. After 1 hr stirring at room temperature, the reaction mixture was cooled with ice. Benzyl chloride (0.5 ml) was added to the mixture and the whole was stirred for 1 hr. The reaction mixture was extracted with ether. The ethereal layer was washed with sat. aq. sodium hydrogen carbonate and sat. aq. sodium chloride, and then dried over sodium sulfate. After removal of the solvent by distillation, the residual oil was heated at 60° C. under vacuum to remove benzyl chloride and 94 mg of 5-benzylthio-1,2,3-thiadiazole was obtained as orange crystals (yield 45%).

Workup

  1. temperaturethe reaction mixture was cooled with ice
  2. stirringthe whole was stirred for 1 hr
  3. extractionThe reaction mixture was extracted with ether
  4. washThe ethereal layer was washed with sat. aq. sodium hydrogen carbonate and sat. aq. sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent
  7. distillationby distillation
  8. temperaturethe residual oil was heated at 60° C. under vacuum
  9. customto remove benzyl chloride

Sources & evidence

ORD record
ord-d6f588ef9ff845e0b9f96994edbb1901
Source dataset
uspto-grants-1985_09
Patent number
US04540794

Reaction notes

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