Water → 4-Chloro-7-methylquinazoline

HRID 1432844

반응식

HRID 1432844 반응식
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:22])=O.O>C1(C)C=CC=CC=1>[Cl:22][C:6]1[C:5]2[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][N:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354525337-Methyl-4(3H)-quinazolinone

생성물 1

HCID 219420144-Chloro-7-methylquinazoline

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a solution of 7-methyl-3H-quinazolin-4-one (10.6 g, 69 mmol) in toluene (350 mL) is added triethylamine (17.5 g, 173 mmol) followed by phosphorous oxychloride (12.3 g, 80 mmol). The resulting solution is heated to 80° C. After 4 hours, the solution is cooled to ambient temperature. The reaction mixture is poured into 500 mL of water. The layers are separated and the organic layer is washed with H2O, saturated NaHCO3, and saturated NaCl, dried over MgSO4, filtered and concentrated. The resulting crude product is purified by recrystallization from EtOAc. The title compound is obtained as a white solid (10 g, 56 mmol). 1H NMR (CDCl3, 300 MHz) δ9.02 (s, 1H), 8.16 (d, 1H), 7.87 (s, 1H), 7.55 (d, 1H), 2.62 (s, 3H).

후처리

  1. temperaturethe solution is cooled to ambient temperature
  2. customThe layers are separated
  3. washthe organic layer is washed with H2O, saturated NaHCO3, and saturated NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude product is purified by recrystallization from EtOAc

출처 및 근거

ORD 기록
ord-c99e29bc5508448993712c48483b72e9
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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