Thionyl Chloride → Bicyclo[2.2.1]hept-7-yl acetyl chloride

HRID 461987

반응식

HRID 461987 반응식
[CH:1]12[CH:7]([CH2:8][C:9]([OH:11])=O)[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S(Cl)([Cl:14])=O>>[CH:1]12[CH:7]([CH2:8][C:9]([Cl:14])=[O:11])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 21392682(Bicyclo[2.2.1]heptan-7-yl)acetic acid

생성물 1

HCID 21392665Bicyclo[2.2.1]hept-7-yl acetyl chloride

반응 조건

온도
50 °C

실험 절차

0.0455 Mole of bicyclo[2.2.1]hept-7-yl acetic acid is mixed with 20 ml. of thionyl chloride at room temperature and allowed to stand for 2 hours. The mixture is then warmed to 50° C and maintained at this temperature for another 2 hours. Excess thionyl chloride is then removed by distillation, under reduced pressure, affording a crude bicyclo[2.2.1]hept-7-yl acetyl chloride residue which is then dissolved in 50 ml. of ethyl ether and added dropwise to a concentrated aqueous ammonia solution (20 ml. of 58% wt. ammonia) at 0° C with rapid stirring. 200 Ml. of ethyl acetate is then added and the resulting mixture stirred. The organic layer is then decanted off and washed twice with water, dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated to dryness, under vacuum, affording bicyclo[2.2.1]hept-7-yl acetamide.

후처리

  1. customat room temperature
  2. temperaturemaintained at this temperature for another 2 hours
  3. customExcess thionyl chloride is then removed by distillation, under reduced pressure

출처 및 근거

ORD 기록
ord-2acbc3974f8b48fc952c6d46d4258a94
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04064258

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