Benzyl mercaptan → 4-(Benzylsulfanyl)-1,3-thiazole

Benzylmercaptan (24.8 g) was added slowly to a solution of 10.8 g of sodium methoxide in 100 ml ethanol. After 10 minutes, the reaction mixture was heated to 65° and a solution of 23.8 g of 4-chlorothiazole [prepared by the method of P. Reynaud et al., Bull. Soc. Chim. France, 1735 (1962)] in 25 ml ethanol was added dropwise. When addition was complete, the reaction mixture was refluxed 36 hours. The reaction mixture was cooled, and the bulk of the solvent evaporated. Cold water (300 ml) was added to the residue, and the aqueous mixture was extracted with 200 ml ether followed by 200 ml methylene chloride. The combined organic solution was washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated. Distillation of the resulting yellow oil gave 15.6 g of 4-(phenylmethylthio)thiazole, bp 122-134 (0.6 mm).

1. temperaturethe reaction mixture was heated to 65°
2. additionWhen addition
3. temperaturethe reaction mixture was refluxed 36 hours
4. temperatureThe reaction mixture was cooled
5. customthe bulk of the solvent evaporated
6. additionCold water (300 ml) was added to the residue
7. extractionthe aqueous mixture was extracted with 200 ml ether
8. washThe combined organic solution was washed with brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. customthe solvent evaporated
12. distillationDistillation of the resulting yellow oil

ORD record

ord-79133d08ab234ddbaf2a479eadc656fc

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04943312