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

HRID 266122ノート

反応式

HRID 266122 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-37045bb94f43476c897b4c3d1d45681e
出典データセット
uspto-grants-1997_07
特許番号
US05650410

反応ノート

読み込み中…