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

HRID 452909

반응식

HRID 452909 반응식
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[Cl:19][CH2:20][C:21](Cl)=O>C(O)(=O)C>[Cl:18][C:14]1[CH:15]=[CH:16][CH:17]=[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[F:13])[C:21]([CH2:20][Cl:19])=[N:1]2

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 223165802-amino-6-chloro-N-(2-fluorophenyl)benzamide

생성물 1

HCID 223165575-Chloro-2-chloromethyl-3-(2-fluorophenyl)-3H-quinazolin-4-one수율 40%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Prepared according to Procedure B with 1k (1.0 g, 3.78 mmol) and chloroacetyl chloride (0.90 mL, 11.3 mmol) in acetic acid (20 mL). Purified by chromatography in CH2Cl2 to afford 484 mg of a pale pink solid (40%). 1H NMR (CDCl3) δ: 7.69 (s, 1H); 7.68 (d, J=3.2 Hz, 1H); 7.56 (d, J=3.0 Hz, 1H); 7.54 (d, J=3.0 Hz, 1H); 7.40-7.47 (m, 1H); 7.35-7.38 (m, 1H); 7.27-7.32 (m, 1H); 4.35 (d, J=12 Hz, 1H); 4.18 (d, J=12 Hz, 1H). MS (ES): m/z 323.0 (M+).

후처리

  1. customPrepared
  2. customPurified by chromatography in CH2Cl2

출처 및 근거

ORD 기록
ord-8d63569829fc483aa140d11f1730c1dc
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492389B2

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