Acetylacetone → HCID 90412515, 화합물

HRID 573943

반응식

HRID 573943 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(=O)[CH2:34][C:35](=[O:37])[CH3:36]>CS(C)=O.[Cu]I>[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH:11]=[N:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH2:34][C:35](=[O:37])[CH3:36])=[CH:3][CH:4]=3)=[N:9]2)=[CH:14][CH:15]=1

참가 물질

6

반응물 3

HCID 31261AcetylacetoneHCID 62657Potassium Phosphate, TribasicHCID 904040773-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazole

생성물 1

HCID 90412515HCID 90412515, 화합물수율 35.3%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
110 °C

실험 절차

3-(4-Bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C52) (11 g, 29 mmol), copper(I) iodide (0.55 g, 2.9 mmol), potassium phosphate (18 g, 86 mmol), and pentane-2,4-dione (8.9 mL, 86 mmol) were dissolved in dimethylsulfoxide (120 mL) in a 500 mL round bottomed flask. The reaction was heated at 110° C. for 19 hours. The solution was cooled to room temperature and then quenched with hydrogen chloride (2 N). The excess base was removed by gravity filtration and the filtrate was extracted with ethyl acetate. The organics were washed with water, extracted, dried, and concentrated. Purification by flash column chromatography using 0-30% ethyl acetate/hexanes afforded the title compound as a pure orange solid (3.7 g, 35%): 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.17 (d, J=8.2 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H), 7.39 (dt, J=8.1, 1.0 Hz, 2H), 7.33 (dd, J=8.1, 0.6 Hz, 2H), 3.76 (s, 2H), 2.19 (s, 3H); ESIMS m/z 361 ([M]+).

후처리

  1. temperatureThe solution was cooled to room temperature
  2. customquenched with hydrogen chloride (2 N)
  3. customThe excess base was removed by gravity filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe organics were washed with water
  6. extractionextracted
  7. customdried
  8. concentrationconcentrated
  9. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-f8711a210c5043c3aac2ff4b91a740c7
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029560B2

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