4,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedione → 2-(5-Furan-2-yl-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid

HRID 649817

반응식

HRID 649817 반응식
[F:1][C:2]([F:14])([F:13])[C:3](=O)[CH2:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[NH:15]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])[NH2:16]>C(O)(=O)C.CCOC(C)=O>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[N:15]([C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])[N:16]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=1

참가 물질

5

반응물 2

HCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 792232-Hydrazinobenzoic acid

생성물 1

HCID 114159972-(5-Furan-2-yl-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

실험 절차

4,4,4-Trifluoro-1-(2-furyl)-1,3-butanedione (2.4 mL, 16 mmol) was added to 2-hydrazinobenzoic acid (3.01 g, 16 mmol) in acetic acid (20 mL) and heated at reflux for 25 h. The reaction was cooled, diluted with EtOAc, and extracted twice with water. The organic layer was dried over Na2SO4, filtered, and evaporated to yield a thick red paste (5.71 g, >100%). 1H NMR (CDCl3) δ8.18 (dd, 1H, J=7.7, J′=1.8), 7.74 (td, 1H, J=7.7, J′=1.4), 7.65 (td, 1H, J=7.7, J′=1.5), 7.50 (dd, 1H, J=7.3, J′=1.1), 7.35 (m, 1H), 6.89 (s, 1H), 6.28 (m, 1H), 5.76 (d, 1H, J=3.3).

후처리

  1. temperatureheated
  2. temperatureat reflux for 25 h
  3. temperatureThe reaction was cooled
  4. extractionextracted twice with water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a thick red paste (5.71 g, >100%)

출처 및 근거

ORD 기록
ord-db6e33ec60db41e0b3064a86bc5b5335
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271237B1

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