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N,N-Dimethylaniline → 6-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline

HRID 2079292
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HRID 2079292 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:23].CN(C)C1C=CC=CC=1>C1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[N:6]=[C:5]2[Cl:23]
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참가 물질

6

반응물 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1361214046-Bromo-2-(2-methoxy-phenyl)-3h-quinazolin-4-one

생성물 1

HCID 580109046-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

실험 절차

6-Bromo-2-(2-methoxyphenyl)quinazolin-4(3H)-one (674 mg, 2.0 mmol), POCl3 (624 mg, 4 mmol), and N,N-dimethylaniline (740 mg, 6.1 mmol) were dissolved in benzene (12 mL) and refluxed for 3 h. The reaction mixture was diluted with EtOAc, and the organic phase was washed with aqueous saturated NaHCO3 (1×) and H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0-5% EtOAc in CH2Cl2/hexanes (1:1) gave 6-bromo-4-chloro-2-(2-methoxyphenyl)quinazoline. LC/MS: m/z 348.9 (M+H)+ at 3.66 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. temperaturerefluxed for 3 h
  2. washthe organic phase was washed with aqueous saturated NaHCO3 (1×) and H2O (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification via silica gel chromatography

출처 및 근거

ORD 기록
ord-bc610a5237e8420b986884c2c6aeb877
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928107B2

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