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

HRID 261563ノート

反応式

HRID 261563 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-de4906c2a94047a598554ec71d34152d
出典データセット
uspto-grants-1979_08
特許番号
US04166127

反応ノート

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