Chloroacetyl chloride → 5-Chloro-2-chloromethyl-3-(2-methoxyphenyl)-3H-quinazolin-4-one

HRID 392256

반응식

HRID 392256 반응식
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].[Cl:20][CH2:21][C:22](Cl)=O>C(O)(=O)C>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:2]2[C:3]=1[C:4](=[O:5])[N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:22]([CH2:21][Cl:20])=[N:1]2

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 223165492-amino-6-chloro-N-(2-methoxyphenyl)benzamide

생성물 1

HCID 223165905-Chloro-2-chloromethyl-3-(2-methoxyphenyl)-3H-quinazolin-4-one수율 28%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Prepared according to Procedure B with 1l (2.6 g, 9.41 mmol) and chloroacetyl chloride (2.2 mL, 28.2 mmol) in acetic acid (40 mL). Purified by chromatography in CH2Cl2, followed by recrystallization from isopropanol to afford 874 mg of a pale yellow solid (28%). 1H NMR (CDCl3) δ: 7.55-7.74 (m, 2H); 7.47-7.54 (m, 2H); 7.34 (dd, J=1.7, 7.8 Hz, 1H); 7.13 (dt, J=1.2, 7.7 Hz, 1H); 7.08 (dd, J=1.0, 8.4 Hz, 1H); 4.29 (d, J=12 Hz, 1H); 4.11 (d, J=12 Hz, 1H); 3.80 (s, 3H). MS (ES): m/z 335.0 (M+).

후처리

  1. customPrepared
  2. customPurified by chromatography in CH2Cl2
  3. customfollowed by recrystallization from isopropanol

출처 및 근거

ORD 기록
ord-8419a8c3016949a6a5248f66c05fa296
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800620B2

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