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

HRID 622866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622866
[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

Komponenten

7

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysatorHCID 1140TolueneLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-64442648381b48e29a34ca78e66e598d
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04772730

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