Toluene → 1,2-Dihydroquinazoline

HRID 472150노트

반응식

HRID 472150 반응식
[C:1]1(C)C=CC=CC=1.Br[C:9]1[CH:10]=[CH:11][C:12]([NH2:17])=[C:13]([CH:16]=1)[CH2:14][NH2:15]>CCOC(C)=O>[NH:17]1[C:12]2[C:13](=[CH:16][CH:9]=[CH:10][CH:11]=2)[CH:14]=[N:15][CH2:1]1

참가 물질

4

반응물 2

HCID 1140TolueneHCID 229568372-(Aminomethyl)-4-bromoaniline

생성물 1

HCID 125313371,2-Dihydroquinazoline

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To toluene (200 mL), 5-bromo-2-amino-benzylamine (9.5 g, 47.2 mmol) and trimethylbenzoic orthoester (8.2 g, 47.2 mmol) were added, followed by p-toulensulfonic acid (1.35 g, 7.1 mmol). The resulting suspension was stirred at reflux for 50 hours. The reaction mixture was cooled at r.t., diluted with AcOEt (150 mL), washed with saturated sodium bicarbonate, then with water. The organic layer was dried and concentrated to provide the intermediate dihydroquinazoline as a light brown solid (8.5 g; 63%). This intermediate is dissolved in DCM (20 mL) at r.t., then MnO2 (5.1 g) was added. The resulting mixture was stirred at r.t. for 48 hrs, then filtered on celite. The filtrate was concentrated to provide the title product as white solid (8.1 g, 95%). C14H9BrN2; MW: 285.15; MS m/z: 286 (M+1). 1H-NMR (300 MHz, d6-DMSO) ppm: 7.58-7.61 (m, 3H), 8.02 (d, 1H), 8.17 (dd, 1H), 8.49-8.56 (m, 3H), 9.70 (s, 1H).

후처리

  1. temperatureat reflux for 50 hours
  2. washwashed with saturated sodium bicarbonate
  3. customThe organic layer was dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-25a11194e9ad429196f2ec263c583192
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633208B2

반응 노트

불러오는 중…