Potassium Carbonate → 2-(4,4-Difluorobut-3-enylthio)benzthiazole

온도

55 °C

To the solution of 4-bromo-1,1-difluorobut-1-ene prepared in Example 6 was added potassium carbonate (10.76 g) and 2-mercaptobenzthiazole (9.18 g). The mixture was stirred at 55° C. for 6 hours and then at room temperature overnight. Gas-liquid chromatography of a sample of the reaction mixture showed that a small amount of 4-bromo-1,1-difluorobut-1-ene remained. More potassium carbonate (1.0 g) was added and the mixture heated for another two and a half hours at 55° C., when all of the bromo compound had been consumed. The mixture was cooled to room temperature and filtered. The residue was washed with acetone and the filtrate and washings combined and evaporated under reduced pressure to give the crude product (16.18 g). This was dissolved in dichloromethane. The solution was filtered and washed with dilute sodium hydroxide (2×25 ml) and with brine (2×25 ml), dried over magnesium sulphate, filtered, the filtrate evaporated to give 2-(4,4-difluorobut-3-enyl)thiobenzthiazole, having a gas chromatographic retention time identical with that of an authentic sample. The yield was 63% based on the quantity of 1,4-dibromo-1,1,2-trifluorobutane used in step (b) of Example 1. 2-(4,4-Difluorobut-3-enyl)thiobenzoxazole was prepared in the same way, but using 2-mercapto benzoxazole instead of 2-mercapto benzthiazole.

1. customat room temperature
2. customovernight
3. temperaturethe mixture heated for another two and a half hours at 55° C.
4. customwhen all of the bromo compound had been consumed
5. temperatureThe mixture was cooled to room temperature
6. filtrationfiltered
7. washThe residue was washed with acetone
8. customevaporated under reduced pressure
9. customto give the crude product (16.18 g)
10. filtrationThe solution was filtered
11. washwashed with dilute sodium hydroxide (2×25 ml) and with brine (2×25 ml)
12. dry with materialdried over magnesium sulphate
13. filtrationfiltered
14. customthe filtrate evaporated

ORD 기록

ord-6da0a75747c440579672b925c643cf74

출처 데이터셋

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05914423