Thiophenol → 4-Methyl-5-[(phenylthio)methyl]-1,2,3-thiadiazole

HRID 1250199Notes

Reaction equation

HRID 1250199 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:7]=[N:8][S:9][C:10]=1[CH2:11]O.C(=O)([O-])[O-].[K+].[K+].[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH3:5][C:6]1[N:7]=[N:8][S:9][C:10]=1[CH2:11][S:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 18411623(4-Methyl-1,2,3-thiadiazol-5-yl)methanol

Product 1

HCID 159066404-Methyl-5-[(phenylthio)methyl]-1,2,3-thiadiazoleYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

At an ice-cooled temperature, 3 ml of thionyl chloride was added to 0.50 g (3.8 mmol) of 4-methyl-1,2,3-thiadiazol-5-ylmethanol and stirred for 4 hours. Then, the reaction mixture was concentrated under reduced pressure, and 1.30 g (11.5 mmol) of potassium carbonate, 0.38 g (3.4 mmol) of thiophenol and 10 ml of acetone were added to the concentrate and reacted for 7 hours with heating under reflux. After the reaction was completed, the reaction mixture was cooled to room temperature, the precipitated matter was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 5:1 mixture of n-hexane and ethyl acetate. Thus, 0.64 g of the objective compound was obtained.

Workup

  1. additionwere added to the
  2. concentrationconcentrate
  3. customreacted for 7 hours
  4. temperaturewith heating
  5. temperatureunder reflux
  6. filtrationthe precipitated matter was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography
  9. addition5:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-7b27486e4e0c4ef7bdc092a413e8d95d
Source dataset
uspto-grants-2002_01
Patent number
US06337341B1

Reaction notes

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