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

HRID 35693노트

반응식

HRID 35693 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 8471Triethylamine촉매HCID 1140Toluene용매2회HCID 3283Diethyl Ether용매2회

실험 절차

A solution of 0.75 g (0.0036 mole) 5-amino-2,3-dihydro-2,2,3,3-tetrafluorobenzofuran 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-(2,3-dihydro-2,2,3,3-tetrafluorobenzofuran-5-yl)-3-(4-difluoromethoxyphenyl)-4-phenylpyrazoline-1-carboxamide (mp 155°-159° C.).

후처리

  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

출처 및 근거

ORD 기록
ord-e27e3875d6524434a03c7d293d973f05
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767779

반응 노트

불러오는 중…