Ethyl orthoformate → 4(3H)-Quinazolinone, 3-(3-bromo-2-methylphenyl)-2-methyl-

HRID 1811012

반응식

HRID 1811012 반응식
[CH3:1][C:2]1O[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C(OC(OCC)OCC)C>C1COCC1.C(Cl)Cl>[Br:13][C:14]1[C:15]([CH3:21])=[C:16]([N:17]2[C:4](=[O:12])[C:5]3[C:6](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:7]=[C:2]2[CH3:1])[CH:18]=[CH:19][CH:20]=1

참가 물질

6

반응물 3

HCID 31214Ethyl orthoformateHCID 68236AcetanthranilHCID 1235383-Bromo-o-toluidine

생성물 1

HCID 633694(3H)-Quinazolinone, 3-(3-bromo-2-methylphenyl)-2-methyl-수율 20%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-methyl-4H-benzo[d][1,3]oxazin-4-one (300 mg, 1.862 mmol), 3-bromo-2-methylaniline (346 mg, 1.862 mmol), and triethoxymethane (276 mg, 1.862 mmol) in THF (2 mL) was heated overnight in a sealed tube at 100° C. The mixture was cooled to rt and diluted with DCM. The solution was washed with water and NaHCO3 (aq), and dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 50:50 hexane-EtOAc) and the crude product was triturated in hexane to give 3-(3-bromo-2-methylphenyl)-2-methylquinazolin-4(3H)-one as an off-white solid (120 mg, 20%). 1H NMR (400 MHz, chloroform-d) δ 8.28 (1 H, dd, J=7.92, 1.10 Hz), 7.77-7.82 (1 H, m), 7.68-7.73 (2 H, m), 7.47-7.52 (1 H, m), 7.22-7.25 (1 H, m), 7.13-7.17 (1 H, m), 2.20 (6H, s). Mass spectrum m/z 329, 331 (M+H)+.

후처리

  1. washThe solution was washed with water and NaHCO3 (aq)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (
  5. washeluting with a gradient from 90:10 to 50:50 hexane-EtOAc) and the crude product
  6. customwas triturated in hexane

출처 및 근거

ORD 기록
ord-f4b029a191074d4d9cb69579b372c9b5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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