Acetic Acid → HCID 33777858, 화합물

온도

80 °C

To a suspension of 1.00 g (7.86 mmol) of 4-cyanotetrahydrothiophenone in 6 mL of ethanol was added 0.275 mL (286 mg, 4.76 mmol) of glacial acetic acid, followed by 0.475 mL (489 mg, 9.77 mmol) of hydrazine hydrate. The resulting clear solution was stirred overnight under nitrogen with heating in an oil bath at 80° C. The cooled reaction mixture was then partitioned between ethyl acetate and saturated sodium bicarbonate aqueous solution. The aqueous phase was re-extracted with an additional portion of ethyl acetate. The combined organic fractions were washed with saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate, filtered, and concentrated to a syrup. Trituration of this oil with dichloromethane containing a small amount (less than 3%) of methanol resulted in crystallization. The suspension was heated to gentle reflux for a few minutes and then cooled. The solid was collected on a filter and washed with a small volume of dichloromethane to yield the title compound as almost colorless crystals. LC-MS 142 (M+1).

1. customThe cooled reaction mixture
2. customwas then partitioned between ethyl acetate and saturated sodium bicarbonate aqueous solution
3. extractionThe aqueous phase was re-extracted with an additional portion of ethyl acetate
4. washThe combined organic fractions were washed with saturated sodium chloride aqueous solution
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to a syrup
8. customTrituration of this oil with dichloromethane containing a small amount (less than 3%) of methanol resulted in crystallization
9. temperatureThe suspension was heated
10. temperatureto gentle reflux for a few minutes
11. temperaturecooled
12. customThe solid was collected on
13. filtrationa filter
14. washwashed with a small volume of dichloromethane

ORD 기록

ord-bb3547642c8043b1a60bfba35dd18e50

출처 데이터셋

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07956061B2