Ammonium Acetate → 4-(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)-quinazolinone

HRID 1788051ノート

反応式

HRID 1788051 の反応式
[NH4+:1].C([O-])(=O)C.ClC(Cl)(Cl)[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][C:12]=1[C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=1)=[O:9]>CS(C)=O>[Cl:34][C:30]1[CH:29]=[C:28]([C:27]2[C:12]3[C:11](=[CH:16][CH:15]=[C:14]([C:17](=[O:26])[C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[CH:13]=3)[NH:10][C:8](=[O:9])[N:1]=2)[CH:33]=[CH:32][CH:31]=1

参加物

4

反応物 2

HCID 517165Ammonium AcetateHCID 179760992,2,2-trichloro-N-[2-(3-chlorobenzoyl)-4-(4-methoxybenzoyl)phenyl]-acetamide

生成物 1

HCID 686894594-(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)-quinazolinone収率 77.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

Acetic acid, ammonium salt (0.107 mol) was added at room temperature to a mixture of intermediate 12 (0.0536 mol) in DMSO (250 ml). The mixture was stirred at 60° C. for 4 hours then brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water and taken up in warm CH3CN. The precipitate was filtered, washed with diethyl ether and dried under a vacuo, yielding 16.2 g (77%) of intermediate 13. The mother layer was evaporated. The residue was purified by column chromatography over silica gel (15-40 μm) (eluent: DCM/MeOH/NH4OH; 95/5/0.1). The pure fractions were collected and the solvent was evaporated. The residue (1.2 g, 6%) was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.9 g (4%) of 4-(3-chlorophenyl)-6-(4-methoxybenzoyl)-2(1H)quinazolinone (intermediate 13), mp. 248° C.

後処理

  1. customthen brought to room temperature
  2. stirringstirred
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. filtrationThe precipitate was filtered
  6. washwashed with diethyl ether
  7. customdried under a vacuo

出典と根拠

ORDレコード
ord-0577cb35c37947539e65a4f808a902ca
出典データセット
uspto-grants-2009_03
特許番号
US07511138B2

反応ノート

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