Chloroacetyl chloride → 6-Bromo-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one

HRID 467895

반응식

HRID 467895 반응식
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][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>[Br:18][C:15]1[CH:14]=[C:3]2[C:2](=[CH:17][CH:16]=1)[N:1]=[C:21]([CH2:20][Cl:19])[N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[C:4]2=[O:5]

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 223165482-amino-5-bromo-N-(2-chlorophenyl)benzamide

생성물 1

HCID 223165756-Bromo-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one수율 83%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Prepared according to Procedure B with 1b (500 mg, 1.54 mmol) and chloroacetyl chloride (0.37 mL, 4.61 mmol) in acetic acid (10 mL). Purified by recrystallization from isopropanol to afford 490 mg of an off-white solid (83%). 1H NMR (CDCl3) δ: 8.43 (d, J=2.3 Hz, 1H); 7.91 (dd, J=2.3, 8.7 Hz, 1H); 7.67 (d, J=8.7 Hz, 1H); 7.60-7.65 (m, 1H); 7.47-7.56 (m, 2H); 7.52 (t, J=5.3 Hz, 1H); 7.47-7.56 (m, 1H); 4.37 (d, J=12 Hz, 1H), 4.06 (d, J=12 Hz, 1H). MS (ES): m/z 385.0 (M+).

후처리

  1. customPrepared
  2. customPurified by recrystallization from isopropanol

출처 및 근거

ORD 기록
ord-bc503e4b4f7a4207a044ebd76cdf91c1
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623881B2

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