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

HRID 631257

反応式

HRID 631257 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
125 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-bd76335f28a84b6c96c4d33b08f4f83e
出典データセット
uspto-grants-2016_04
特許番号
US09320739B2

関連ノート

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