Chloroacetyl chloride → 5-Chloro-2-chloromethyl-3-o-tolyl-3H-quinazolin-4-one

HRID 241911

반응식

HRID 241911 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[CH3:13])=[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[CH3:13])[C:21]([CH2:20][Cl:19])=[N:1]2

참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 124873672-Amino-6-chloro-N-o-tolylbenzamide

생성물 1

HCID 124873735-Chloro-2-chloromethyl-3-o-tolyl-3H-quinazolin-4-one수율 37%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Prepared according to Procedure B with 1j (750 mg, 2.88 mmol) and chloroacetyl chloride (0.69 mL, 8.63 mmol) in acetic acid (15 mL). Purified by chromatography in CH2Cl2, followed by recrystallization from isopropanol to afford 340 mg of a white solid (37%). 1H NMR (CDCl3) δ: 7.69 (d, J=2.1 Hz, 1H); 7.68 (q, J=7.4 Hz, 1H); 7.54 (dd, J=2.2, 7.0 Hz, 1H); 7.35-7.47 (m, 3H); 7.21-7.25 (m, 1H); 4.27 (d, J=12 Hz, 1H); 4.11 (d, J=12 Hz, 1H); 2.18 (s, 3H). MS (ES): m/z 319.0 (M+).

후처리

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

출처 및 근거

ORD 기록
ord-bd13829226874b17ab82e0b7b324b7f7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653077B2

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