Water → 3-oxo-N-[3-(trifluoromethyl)phenyl]butanamide

HRID 1112040

반응식

HRID 1112040 반응식
O.[C:2]([O:8]CC)(=O)[CH2:3][C:4]([CH3:6])=[O:5].C1(C)C(C)=CC=CC=1.[NH2:19][C:20]1[CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1>CCCCCC>[F:27][C:26]([F:28])([F:29])[C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[NH:19][C:2](=[O:8])[CH2:3][C:4]([CH3:6])=[O:5]

참가 물질

6

반응물 4

HCID 962WaterHCID 7237O-Xylene2회HCID 73753-(Trifluoromethyl)anilineHCID 8868Ethyl Acetoacetate

생성물 1

HCID 7443663-oxo-N-[3-(trifluoromethyl)phenyl]butanamide수율 55.7%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

A two-liter reaction flask fitted with a magnetic stirrer, heating mantle, dropping funnel, thermometer, water-cooled condenser and Dean Stark trap was charged with 156.2 g (1.2 moles) of ethyl acetoacetate and 400 ml of xylene. The dropping funnel contained 161 g (1.0 mole) of 3-aminobenzotrifluoride and 320 ml xylene. The solution in the reaction pot was heated to 135° and the contents of the dropping funnel were added dropwise over a period of 3 hours. The low-boiling liquid which accumulated in the Dean Stark trap was periodically drained in order to maintain a reaction temperature of about 135°. After 4 hours, the reaction was judged to be completed and the reaction solution was cooled. There was added 650 ml of hexane. Cooling in an ice bath yielded a white crystalline precipitate. The product was collected on a vacuum filter and dried in an oven. There was obtained 136.6 g (55.7%) of 3'-trifluoromethylacetoacetanilide, m.p. 109°-10°. N.M.R. (CDCl3) ∂ 2.2 (CH3, keto), 3.5 (CH2), 7.2-7.9 (aromatic), 1.8 (CH3, enol).

후처리

  1. customA two-liter reaction flask
  2. customfitted with a magnetic stirrer
  3. temperatureheating mantle
  4. customThe solution in the reaction
  5. temperaturepot was heated to 135°
  6. additionthe contents of the dropping funnel were added dropwise over a period of 3 hours
  7. temperatureto maintain a reaction temperature of about 135°
  8. temperaturethe reaction solution was cooled
  9. temperatureCooling in an ice bath
  10. customyielded a white crystalline precipitate
  11. customThe product was collected on a vacuum
  12. filtrationfilter
  13. customdried in an oven

출처 및 근거

ORD 기록
ord-da0fea2e50394fe29f272734f3d3f22e
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04120690

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