Phosphorus oxychloride → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinazoline

HRID 631257

반응식

HRID 631257 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](O)=[N:11][CH:12]=[N:13]2)=[CH:8][C:7]=1[O:17][CH3:18].P(Cl)(Cl)([Cl:21])=O>C1(C)C=CC=CC=1>[Cl:21][C:10]1[C:9]2[C:14](=[CH:15][C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[C:7]([O:17][CH3:18])[CH:8]=2)[N:13]=[CH:12][N:11]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 1784867697-(3-chloropropoxy)-6-methoxy-1H-quinazolin-4-one

생성물 1

HCID 574472274-Chloro-7-(3-chloropropoxy)-6-methoxyquinazoline수율 78%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
125 °C

실험 절차

To a solution of the intermediate from Step 4 (3.00 g, 11.16 mmol) in toluene (30 mL) in a pressure vessel was added phosphorous oxychloride (8 mL). The mixture was heated to 125° C. for 5 hours. Completion of the reaction was monitored by LCMS. The mixture was concentrated to dryness and excess ethyl acetate was added. The solution was washed with water and brine and was dried (Na2SO4) and concentrated to afford the pure compound 4-chloro-7-(3-chloro-propoxy)-6-methoxy-quinazoline (2.51 g, 78%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.85 (s, 1H), 7.48 (s, 1H), 7.35 (s, 1H), 4.35 (t, 2H), 4.00 (s, 3H), 3.75 (t, 2H), 2.25 (q, 2H). LC-MS (ESI)m/z 287 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated to dryness and excess ethyl acetate
  2. additionwas added
  3. washThe solution was washed with water and brine
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bd76335f28a84b6c96c4d33b08f4f83e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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