Carbon Disulfide → 3-{2-[(2-Hydroxyethyl)sulfanyl]ethyl}-4-methyl-1,3-thiazole-2(3H)-thione

Temperature

0 °C

In 500 ml of ethanol, 24.2 g of (2) and 24.7 ml of triethylamine were dissolved and cooled to 0° C. Thereto, 16.8 g of carbon disulfide was added dropwise. The resulting mixture was allowed to stand for 2 hours at a room temperature and further, for an additional 30 minutes at 50° C. to conduct the reaction. Then, the reaction mixture was cooled to 0° C. again. Thereto, 19.4 g of chloroacetone was added dropwise. The reaction was run by keeping the temperature of the reactionsystem at a room temperature for 1 hour and further, at 40° C. for an additional 2 hours. At the conclusion of the reaction, the solvent was removed by distillation under reduced pressure, and water was added to the residue. The reaction product was extracted with ethyl acetate, washed with water three times, and dried over anhydrous sodium sulfate. Upon the removal of ethyl acetate from the extract by distillation, (1) was obtained as an oily sub stance.

1. waitfurther, for an additional 30 minutes at 50° C. to conduct
2. customthe reaction
3. temperatureThen, the reaction mixture was cooled to 0° C. again
4. customat a room temperature
5. customfor 1 hour
6. waitfurther, at 40° C. for an additional 2 hours
7. customAt the conclusion of the reaction
8. customthe solvent was removed by distillation under reduced pressure, and water
9. additionwas added to the residue
10. extractionThe reaction product was extracted with ethyl acetate
11. washwashed with water three times
12. dry with materialdried over anhydrous sodium sulfate
13. customUpon the removal of ethyl acetate from the
14. extractionextract by distillation

ORD record

ord-33c03bfc644b4b1c85cfe0d37875d43b

Source dataset

uspto-grants-1985_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04551419