O,O-diethyl phosphorothioate → 4-Hydroxythiobenzamide

HRID 413290

반응식

HRID 413290 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(OP(=[S:18])(O)OCC)C>O>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[S:18])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 655O,O-diethyl phosphorothioateHCID 130194-Cyanophenol

생성물 1

HCID 27593444-Hydroxythiobenzamide수율 87%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
80 °C

실험 절차

In a round bottomed flask, 4-hydroxybenzonitrile (5.00 g, 41.9 mmol), diethylthiophosphoric acid (7.02 g, 41.9 mmol), and water (8 ml) were heated with stirring to about 80° C. for about thirty minutes. An additional 10 ml of water was then added to the suspension, and the reaction was heated for about another one hour. The mixture was then allowed to stir for about sixteen hours at room temperature and was then extracted with water and 1:1 ether/ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by column chromatography (silica gel; hexanes to ethyl acetate). The product was isolated as a yellow solid (5.54 g, 87% yield). 1H NMR (CD3OD): δ6.74 (d, 2H, J=9.1 Hz), 7.83 (d, 2H, J=8.7 Hz).

후처리

  1. temperaturethe reaction was heated for about another one hour
  2. stirringto stir for about sixteen hours at room temperature
  3. extractionwas then extracted with water and 1:1 ether/ethyl acetate
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was purified by column chromatography (silica gel; hexanes to ethyl acetate)

출처 및 근거

ORD 기록
ord-fb6a750646784e30857fbd92161a4257
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566377B2

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