氯乙酰氯 → 2-Chloromethyl-3-(2-chlorophenyl)-5-fluoro-3H-quinazolin-4-one

HRID 241908笔记

反应方程式

HRID 241908 反应方程式
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=[O:5].[Cl:19][CH2:20][C:21](Cl)=O>C(O)(=O)C>[Cl:19][CH2:20][C:21]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:4](=[O:5])[C:3]2[C:2](=[CH:17][CH:16]=[CH:15][C:14]=2[F:18])[N:1]=1

参与物

4

反应物 2

HCID 6577氯乙酰氯HCID 223165682-amino-N-(2-chlorophenyl)-6-fluorobenzamide

产物 1

HCID 223165672-Chloromethyl-3-(2-chlorophenyl)-5-fluoro-3H-quinazolin-4-one收率 70.4%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

Prepared according to Procedure B with 1e (500 mg, 1.89 mmol) and chloroacetyl chloride (0.45 mL, 5.67 mmol) in acetic acid (10 mL). Purified by extraction from aq. K2CO3 and recrystallization from isopropanol to afford 430 mg of an off-white crystalline solid (70%). 1H NMR (CDCl3) δ: 7.76 (dt, J=5.3, 8.2 Hz, 1H); 7.56-7.65 (m, 2H); 7.47-7.56 (m, 3H); 7.16-7.25 (m, 1H); 4.35 (d, J=12 Hz, 1H), 4.07 (d, J=12 Hz, 1H). MS (ES): m/z 323.0 (M+).

后处理

  1. customPrepared
  2. customPurified by extraction from aq. K2CO3 and recrystallization from isopropanol

来源与证据

ORD记录
ord-4926188f0c694731908c918c24a1219d
来源数据集
uspto-grants-2014_02
专利号
US08653077B2

反应笔记

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