Trifluoroacetic acid → 5-(3-dimethylaminopropylidene)-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

HRID 1284251노트

반응식

HRID 1284251 반응식
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][CH2:5][C:6]1(O)[C:12]2[CH:13]=[C:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:21]=[CH:22][CH:23]=[CH:24][C:7]1=2.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>>[CH3:26][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[C:6]1[C:12]2[CH:13]=[C:14]([S:17]([CH3:20])(=[O:18])=[O:19])[CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9][C:8]2[CH:21]=[CH:22][CH:23]=[CH:24][C:7]1=2

참가 물질

5

반응물 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 214120875-(3-dimethylaminopropyl)-5-hydroxy-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

생성물 1

HCID 494065-(3-dimethylaminopropylidene)-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene

반응 조건

온도
70 °C

실험 절차

5-(3-Dimethylaminopropyl)-5-hydroxy-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene (13.62 g., 0.037 mole) is dissolved in 136 ml. of trifluoroacetic acid. Trifluoroacetic anhydride, 68 ml., is added and the solution heated under reflux for 1 hour in a water-bath at 70°C. The dark green solution is cooled and poured into 250 ml. of ice-water. The mixture is rendered alkaline with 10 N. sodium hydroxide solution while stirring and cooling and extracted with benzene. The benzene extract is washed with water, dried over sodium sulfate and the benzene distilled under reduced pressure. The mixed geometric isomers of 5-(3-dimethylaminopropylidene)-3-methylsulfonyl-5H-dibenzo[a,d]cycloheptene is obtained as a brown oily residue in a yield of 13.19 g. (theory, 13.08 g.).

후처리

  1. addition, is added
  2. temperaturethe solution heated
  3. temperatureThe dark green solution is cooled
  4. additionpoured into 250 ml
  5. temperaturecooling
  6. extractionextracted with benzene
  7. extractionThe benzene extract
  8. washis washed with water
  9. dry with materialdried over sodium sulfate
  10. distillationthe benzene distilled under reduced pressure

출처 및 근거

ORD 기록
ord-9574e2e514ea48ae99b3da7bd7e3e1ee
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03978121

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