Benzoyl Peroxide → 4-(Bromomethyl)-6,7-dimethoxyquinazoline

HRID 2063293노트

반응식

HRID 2063293 반응식
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:16][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 43194226,7-Dimethoxy-4-methylquinazoline

생성물 1

HCID 598058494-(Bromomethyl)-6,7-dimethoxyquinazoline

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

4-Methyl-6,7-dimethoxyquinazoline (D-1) (3.43 g, 14.7 mMol), N-bromosuccinimide (NBS) (2.64 g, 14.7 mMol) and benzoyl peroxide (BPO) (500 mg) were heated under reflux in 200 mL of carbon tetrachloride with irradiation by a 200 W sun lamp for 5 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane and extracted twice with water. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. Flash chromatography on silica gel, eluting with hexanes/ethyl acetate gave 4-bromomethyl-6,7-dimethoxyquinazoline (E-1) as a pinkish solid, 1.39 g; 1H NMR (CDCl3, 300 MHz) 9.07 (s, 1H), 7.34 (s, 1H), 7.30 (s, 1H), 4.85 (s, 2H), 4.06 (s, 6H) ppm; 13C NMR (CDCl3, 75 MHz) 161.22, 156.32, 153.45, 150.72, 149.22, 118.85, 107.47, 101.78, 56.84, 56.70, 30.13; MS (ES) 283/285 (M+H).

후처리

  1. extractionextracted twice with water
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. washFlash chromatography on silica gel, eluting with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-3dd1a740d448460fbd6a762cf78885d7
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288382B2

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