Phosphorus oxychloride → 4-Chloro-8-nitroquinazoline

HRID 1469763

반응식

HRID 1469763 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][NH:10][C:9]2=O)([O-:3])=[O:2].O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:9]1[C:8]2[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[N:12]=[CH:11][N:10]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 1354087998-Nitroquinazolin-4-ol

생성물 1

HCID 114584714-Chloro-8-nitroquinazoline

실험 절차

A solution of 8-nitroquinazolin-4(3H)-one (Intermediate-7, step-1, 300 mg, 1.57 mmol) in POCl3 (3 mL) was heated at reflux for 2 h. Then the reaction mixture was concentrated and dried to afford 4-chloro-8-nitroquinazoline which was used for the next step without further purification. Then NaH (263 mg, 11.54 mmol, 95%) was added to EtOH (2 mL) at 0° C. and stirred at that temperature for 15 minutes before it was added to a solution of 4-chloro-8-nitroquinazoline in THF (2 mL) at 0° C. Then the reaction mixture was stirred at rt for 4 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 200 mg of the title product. MS (m/z): 220.23 (M+H)+.

후처리

  1. temperatureat reflux for 2 h
  2. concentrationThen the reaction mixture was concentrated
  3. customdried

출처 및 근거

ORD 기록
ord-2d0ce01831fd49a3bcb2eaf593bee09e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006257B2

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