Phosgene → N-(2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide

HRID 622866ノート

反応式

HRID 622866 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([F:11])([F:10])[C:7]([F:13])([F:12])[C:6]=2[CH:14]=1.[C:15](Cl)(Cl)=[O:16].[F:19][CH:20]([F:39])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[NH:29][NH:30][CH2:31][C:32]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C(OCC)C.C(N(CC)CC)C>[F:11][C:8]1([F:10])[C:7]([F:13])([F:12])[C:6]2[CH:14]=[C:2]([NH:1][C:15]([N:30]3[CH2:31][C:32]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[C:28]([C:25]4[CH:24]=[CH:23][C:22]([O:21][CH:20]([F:19])[F:39])=[CH:27][CH:26]=4)[NH:29]3)=[O:16])[CH:3]=[CH:4][C:5]=2[O:9]1

参加物

7

反応物 3

HCID 6371PhosgeneHCID 137849875-Benzofuranamine, 2,2,3,3-tetrafluoro-2,3-dihydro-HCID 704081453-(4-Difluoromethoxyphenyl)-4-phenylpyrazoline

生成物 1

HCID 86742033N-(2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide

試薬・触媒・溶媒 3

HCID 8471Triethylamine触媒HCID 1140Toluene溶媒2 回HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 0.75 g (0.0036 mole) of the 5-amino-2,2,3,3-tetrafluorobenzofuran of part A, dissolved in 109 ml of toluene, was added dropwise to a stirred solution of 8.0 ml 20% phosgene in toluene. After complete addition the mixture was heated at reflux for two hours. The mixture was cooled and the solvent removed by evaporation under reduced pressure leaving a residue. This residue was dissolved in 15 ml of diethyl ether and added to a stirred solution of 1.04 g (0.0036 mole) 3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline and three drops of triethylamine in 100 ml of diethyl ether. After complete addition the mixture was heated at reflux for one hour, then cooled to room temperature and stirred for approximately 18 hours. The solvent was removed from the reaction mixture by evaporation under reduced pressure leaving a solid residue. Recrystallization from ethanol provided 0.99 g of N-(2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide (mp 155°-159° C.). The nmr spectrum and elemental analysis were consistent with the proposed structure.

後処理

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureat reflux for two hours
  4. temperatureThe mixture was cooled
  5. customthe solvent removed by evaporation under reduced pressure
  6. customleaving a residue
  7. additionAfter complete addition the mixture
  8. temperaturewas heated
  9. temperatureat reflux for one hour
  10. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure
  11. customleaving a solid residue
  12. customRecrystallization from ethanol

出典と根拠

ORDレコード
ord-64442648381b48e29a34ca78e66e598d
出典データセット
uspto-grants-1988_09
特許番号
US04772730

反応ノート

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