N-methyl-2-pyrrolidone → 2-Trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f]thiepin

HRID 261563노트

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HRID 261563 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12](Cl)[C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1.[Cu](C#N)[C:22]#[N:23].CN1CCCC1=O.O.N>S([O-])([O-])(=O)=O.[Cu+2].O>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:18]=[CH:17][C:6]2[S:7][C:8]3[CH:15]=[CH:14][CH:13]=[C:12]([C:22]#[N:23])[C:9]=3[CH2:10][CH2:11][C:5]=2[CH:4]=1

참가 물질

7

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 126871202-Trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepinHCID 12896473Azane;hydrateHCID 178418260HCID 178418260, 화합물

생성물 1

HCID 126871222-Trifluoromethyl-9-cyano-10,11-dihydrodibenzo[b,f]thiepin수율 14.7%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 962Water용매

실험 절차

The mixture of 450 mg of 2-trifluoromethyl-9-chloro-10,11-dihydrodibenzo[b,f]thiepin, 0.4 g of copper cyanide, 0.05 g of anhydrous copper sulfate and 10 ml of N-methylpyrrolidone was stirred at 180° to 210° C. for 18.5 hrs. while preventing the moisture. After cooling, to the mixture was added 2.5 ml of conc. ammonia water and 35 ml of water and the resulting mixture was filtered with the use of celite. The thus obtained solution was extracted with benzene and the extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 0.3 g of a brown oily substance, which was chromatographed on a silica gel, eluted with n-hexane, and there was obtained 64 mg of the desired product. This was recrystallized from n-hexane to afford 2-trifluoromethyl-9-cyano-10,11 -dihydrodibenzo[b,f]thiepin having a melting point of 113° to 114.5° C. as colorless crystals.

후처리

  1. temperatureAfter cooling, to the mixture
  2. filtrationthe resulting mixture was filtered with the use of celite
  3. extractionThe thus obtained solution was extracted with benzene
  4. washthe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customto obtain 0.3 g of a brown oily substance, which
  8. customwas chromatographed on a silica gel
  9. washeluted with n-hexane

출처 및 근거

ORD 기록
ord-de4906c2a94047a598554ec71d34152d
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04166127

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