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Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-3H-benzo[g]quinazolin-4-one

HRID 433253
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HRID 433253 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:20]([NH2:21])=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[O:10].[Cl:22][CH2:23][C:24](Cl)=O>C(O)(=O)C>[Cl:22][CH2:23][C:24]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9](=[O:10])[C:11]2[C:20](=[CH:19][C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:12]=2)[N:21]=1
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참가 물질

4

반응물 2

HCID 6577Chloroacetyl chlorideHCID 612095213-Aminonaphthalene-2-carboxylic acid (2-chlorophen-yl)amide

생성물 1

HCID 223165832-Chloromethyl-3-(2-chlorophenyl)-3H-benzo[g]quinazolin-4-one수율 39%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Prepared according to Procedure B with 1n (500 mg, 1.68 mmol) and chloroacetyl chloride (0.40 mL, 5.05 mmol) in acetic acid (10 mL). Purified by chromatography in CH2Cl2 followed by recrystallization from isopropanol to afford 232 mg of a light-brown solid (39%). 1H NMR (CDCl3) δ: 8.92 (s, 1H); 8.29 (s, 1H); 8.81 (d, J=8.3, 1H); 8.32 (d, J=8.3 Hz, 1H); 7.51-7.69 (m, 4H); 7.55 (d, J=5.2 Hz, 1H); 7.53 (d, J=3.8 Hz, 1H); 4.43 (d, J=12 Hz, 1H), 4.12 (d, J=12 Hz, 1H). MS (ES): m/z 355.0 (M+).

후처리

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

출처 및 근거

ORD 기록
ord-72691081d87c4372bf34488573d4395b
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06667300B2

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