Thionyl Chloride → (3-Methoxyphenyl)acetonitrile

HRID 35598

반응식

HRID 35598 반응식
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]([NH2:16])=O)[CH:10]=[CH:11][CH:12]=1>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH2:13][C:14]#[N:16])[CH:10]=[CH:11][CH:12]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 27749732-(3-Methoxyphenyl)acetamide

생성물 1

HCID 88310(3-Methoxyphenyl)acetonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Thionyl chloride (1249 ml) was added dropwise to dry dimethylformamide (400 ml) stirring at 0°-5° C. under nitrogen over a period of about 2 hours. 3-Methoxyphenylacetamide (403.7 g) was added portionwise over a period of 45 minutes to the above solution under nitrogen maintaining the temperature between 0°-5° C. The reaction mixture was then stirred at 0°-5° C. for a further 2 hours. The reaction mixture was poured carefully onto ice/water (6 l). The aqueous mixture was extracted with ether. The extracts were washed with water, dried over magnesium sulphate and evaporated in vacuo to give a red liquid. The crude product was distilled (110°-112° C./12 mm Hg) to give 3-methoxyphenylacetonitrile.

후처리

  1. stirringThe reaction mixture was then stirred at 0°-5° C. for a further 2 hours
  2. additionThe reaction mixture was poured carefully onto ice/water (6 l)
  3. extractionThe aqueous mixture was extracted with ether
  4. washThe extracts were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated in vacuo
  7. customto give a red liquid
  8. distillationThe crude product was distilled (110°-112° C./12 mm Hg)

출처 및 근거

ORD 기록
ord-9c9dcda28fe244a7982077b1f6608d72
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767769

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