Water → 1-Methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonitrile

HRID 1843065ノート

反応式

HRID 1843065 の反応式
F[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[C:3]=1[C:15]([F:18])([F:17])[F:16].[C-:19]#[N:20].[Na+].O.C(OCC)C>C(#N)C>[C:19]([C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[C:3]=1[C:15]([F:18])([F:17])[F:16])#[N:20]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 135102735-Fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethyl-1H-pyrazole

生成物 1

HCID 866600911-Methyl-3-(perfluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonitrile

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

42.0 g (147 mmol) of 5-fluoro-1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazole [synthesis see Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 1990, (11), 2583-9] and 11.5 g (235 mmol) of sodium cyanide are suspended in 150 ml of acetonitrile and then heated at reflux temperature under a protective gas atmosphere. After cooling, the reaction mixture is poured onto a mixture of 300 ml of distilled water and 300 ml of diethyl ether. The aqueous phase is extracted three times with diethyl ether. The combined organic phases are washed twice with water and once with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and then filtered. The solvent is removed under reduced pressure on a rotary evaporator and the residue obtained in this way is subjected to fractional distillation in vacuo. This gives 37.0 g of 5-cyano-1-methyl-3-pentafluoroethyl-4-trifluoromethylpyrazole (82%) as a colourless liquid (b.p. 74° C./10 mbar).

後処理

  1. temperatureheated
  2. temperatureat reflux temperature under a protective gas atmosphere
  3. temperatureAfter cooling
  4. extractionThe aqueous phase is extracted three times with diethyl ether
  5. washThe combined organic phases are washed twice with water and once with saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase is dried over sodium sulphate
  7. filtrationfiltered
  8. customThe solvent is removed under reduced pressure on a rotary evaporator
  9. customthe residue obtained in this way
  10. distillationis subjected to fractional distillation in vacuo

出典と根拠

ORDレコード
ord-450bcc2f73eb40e99ba2b6752f61e486
出典データセット
uspto-grants-2015_02
特許番号
US08946234B2

反応ノート

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