Benzene → (4-Methyl-1,2,3-thiadiazol-5-yl)(phenyl)methanone

HRID 1250194Notes

Reaction equation

HRID 1250194 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:7]=[N:8][S:9][C:10]=1[C:11]([OH:13])=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:11]([C:10]1[S:9][N:8]=[N:7][C:6]=1[CH3:5])(=[O:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 13819924-Methyl-1,2,3-thiadiazole-5-carboxylic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12298991(4-Methyl-1,2,3-thiadiazol-5-yl)(phenyl)methanoneYield 97%

Procedure

To 2.0 g (15 mmol) of thionyl chloride was added 0.50 g (3.5 mmol) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. After heating the mixture with stirring for 2 hours, the thionyl chloride was distilled off under reduced pressure, and the residue was added to a solution of 1.8 g (15 mmol) of aluminum chloride in 20 ml benzene and made to react with heating for 3 hours. After the reaction was completed, the reaction mixture was poured into ice water, the objective product was extracted with ethyl acetate, the organic layer was washed with a saturated aqueous solution of sodium chloride and dried, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 4:1 mixture of n-hexane and ethyl acetate. Thus, 0.69 g of the objective compound was obtained.

Workup

  1. temperatureAfter heating the mixture
  2. distillationthe thionyl chloride was distilled off under reduced pressure
  3. customto react
  4. temperaturewith heating for 3 hours
  5. extractionthe objective product was extracted with ethyl acetate
  6. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography
  10. addition4:1 mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-8ace731d22a047acb26333990709fc8b
Source dataset
uspto-grants-2002_01
Patent number
US06337341B1

Reaction notes

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