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

HRID 452908

反応式

HRID 452908 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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+).

後処理

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

出典と根拠

ORDレコード
ord-ef8cdc8aa52741e7a7b3ea5820a2dd1d
出典データセット
uspto-grants-2013_07
特許番号
US08492389B2

関連ノート

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