Phosphorus tribromide → 2-(2-Bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline

HRID 266122노트

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HRID 266122 반응식
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[C:17]([CH2:29][CH2:30]O)[N:16]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[Br:2][CH2:30][CH2:29][C:17]1[N:16]=[C:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=2)[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=1

참가 물질

5

반응물 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 220975944-(3,4-Dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline

생성물 1

HCID 220975842-(2-Bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline수율 72.3%

시약·촉매·용매 1

HCID 241Benzene용매

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온도
75 °C

실험 절차

Phosphorus tribromide (PBr3)(0.95 g) was added dropwise to a solution of 4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline (2.6 g) in benzene (50 ml) at room temperature. The mixture was stirred at 75° C. for 1 hour, poured into ice-cold water, neutralized with an aqueous saturated solution of sodium bicarbonate, and then extracted with chloroform. The chloroform layer was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (3:1, v/v) gave 2-(2-bromoethyl)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline (1.1 g, 37%). This was recrystallized from ethyl acetate. Colorless needles, mp. 166°-167° C.

후처리

  1. additionpoured into ice-cold water
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe fractions eluted with chloroform-ethyl acetate (3:1

출처 및 근거

ORD 기록
ord-37045bb94f43476c897b4c3d1d45681e
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650410

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