Chloroacetyl chloride → 2-Chloromethyl-3-(2-chlorophenyl)-5-fluoro-3H-quinazolin-4-one

HRID 452904

反応式

HRID 452904 の反応式
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=[O:5].[Cl:19][CH2:20][C:21](Cl)=O>C(O)(=O)C>[Cl:19][CH2:20][C:21]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:4](=[O:5])[C:3]2[C:2](=[CH:17][CH:16]=[CH:15][C:14]=2[F:18])[N:1]=1

参加物

4

反応物 2

HCID 6577Chloroacetyl chlorideHCID 223165682-amino-N-(2-chlorophenyl)-6-fluorobenzamide

生成物 1

HCID 223165672-Chloromethyl-3-(2-chlorophenyl)-5-fluoro-3H-quinazolin-4-one収率 70.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Prepared according to Procedure B with 1e (500 mg, 1.89 mmol) and chloroacetyl chloride (0.45 mL, 5.67 mmol) in acetic acid (10 mL). Purified by extraction from aq. K2CO3 and recrystallization from isopropanol to afford 430 mg of an off-white crystalline solid (70%). 1H NMR (CDCl3) δ: 7.76 (dt, J=5.3, 8.2 Hz, 1H); 7.56-7.65 (m, 2H); 7.47-7.56 (m, 3H); 7.16-7.25 (m, 1H); 4.35 (d, J=12 Hz, 1H), 4.07 (d, J=12 Hz, 1H). MS (ES): m/z 323.0 (M+).

後処理

  1. customPrepared
  2. customPurified by extraction from aq. K2CO3 and recrystallization from isopropanol

出典と根拠

ORDレコード
ord-21eb5798eccc4cb0bc11e04f4b4912b6
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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