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

HRID 866935ノート

反応式

HRID 866935 の反応式
[CH3:1][N:2]1CCCC1=O.[CH3:8][O:9][C:10]1[CH:25]=[CH:24][C:13]2[S:14][C:15]3[CH:22]=[CH:21][CH:20]=[C:19](Cl)[C:16]=3[CH2:17][CH2:18][C:12]=2[CH:11]=1.[Cu](C#N)C#N.O.N>S([O-])([O-])(=O)=O.[Cu+2].C1C=CC=CC=1.O>[CH3:8][O:9][C:10]1[CH:25]=[CH:24][C:13]2[S:14][C:15]3[CH:22]=[CH:21][CH:20]=[C:19]([C:1]#[N:2])[C:16]=3[CH2:17][CH2:18][C:12]=2[CH:11]=1

参加物

8

反応物 4

HCID 13387N-methyl-2-pyrrolidoneHCID 12896473Azane;hydrateHCID 233370502-Methoxy-9-chloro-10,11-dihydrodibenzo[b,f]thiepinHCID 178418260HCID 178418260、化合物

生成物 1

HCID 233370482-Methoxy-9-cyano-10,11-dihydrodibenzo[b,f]thiepin収率 50%

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

To 100 ml of N-methylpyrrolidone was added 10.8g of 2-methoxy-9-chloro-10,11-dihydrodibenzo[b,f]thiepin, 10.7g of copper cyanide and 0.4g of anhydrous copper sulfate and the resulting mixture was stirred at 190°-195° C for 15 hours. After cooling, to the mixture was added 28% ammonia water, 200 ml of water and 200 ml of benzene and the resulting mixture was shaked and filtered with celite. The filtrate was extracted with benzene. The extract was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and freed of the solvent to obtain 9.0g of light brown cyrstals. This product was chromatographed over silica gel and eluted with benzene, there was obtained 5.4g (50%) of 2-methoxy-9-cyano-10,11-dihydrodibenzo[ b,f]thiepin as colorless prismatic crystals having a melting point of 129°-130° C.

後処理

  1. temperatureAfter cooling, to the mixture
  2. filtrationfiltered with celite
  3. extractionThe filtrate was extracted with benzene
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customto obtain 9.0g of light brown cyrstals
  7. customThis product was chromatographed over silica gel
  8. washeluted with benzene

出典と根拠

ORDレコード
ord-4700ad0dff764d38b8e5dd48ae4e6200
出典データセット
uspto-grants-1978_07
特許番号
US04101667

反応ノート

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