Tetrahydrofuran → 2-(2-Ethylsulfanylphenyl)-4-methyl-7-trifluoromethylquinazoline

HRID 521665

반응식

HRID 521665 반응식
C[Mg]Br.[CH2:4]1COCC1.Cl[C:10]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:17][CH:18]=2)[N:13]=[C:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30][CH2:31][CH3:32])[N:11]=1.CN1C(=O)CCC1>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].O.C(OCC)(=O)C>[CH2:31]([S:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:12]1[N:11]=[C:10]([CH3:4])[C:19]2[C:14](=[CH:15][C:16]([C:20]([F:22])([F:21])[F:23])=[CH:17][CH:18]=2)[N:13]=1)[CH3:32]

참가 물질

8

반응물 4

HCID 8028Tetrahydrofuran2회HCID 13387N-methyl-2-pyrrolidoneHCID 1182058194-Chloro-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazolineHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 1182058222-(2-Ethylsulfanylphenyl)-4-methyl-7-trifluoromethylquinazoline

시약·촉매·용매 3

HCID 5483663Ferric acetylacetonate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

2.1 ml of methylmagnesium bromide (a 1 M THF solution) was added to a mixture of 380 mg of 4-chloro-2-(2-ethylsulfanylphenyl)-7-trifluoromethylquinazoline, 72 mg of iron(III) acetylacetonate, 8 ml of THF and 0.8 ml of NMP, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added to the reaction mixture, and the mixture was filtered. The aqueous layer of the filtrate was extracted with ethyl acetate, combined with the organic layer of the filtrate, sequentially washed with 0.5 N hydrochloric acid, water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 123 mg of 2-(2-ethylsulfanylphenyl)-4-methyl-7-trifluoromethylquinazoline (Compound of Present Invention 13).

후처리

  1. filtrationthe mixture was filtered
  2. extractionThe aqueous layer of the filtrate was extracted with ethyl acetate
  3. washsequentially washed with 0.5 N hydrochloric acid, water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationThe mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-93135b4fd11e4d62bfc95a20d705c658
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328121B1

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