Sodium hydride → HCID 86648969、化合物

HRID 449936ノート

反応式

HRID 449936 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:13]=1[C:14](Cl)=[O:15].CCOCC.CCCCCC>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:14](=[O:15])[C:13]2[C:12]([Cl:11])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:21])[CH:3]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 783922,6-Dichlorobenzoyl chlorideHCID 2380124-Amino-6-chloropyrimidineHCID 21584099Diethylether hexane

生成物 1

HCID 86648969HCID 86648969、化合物収率 64.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution of 6-chloropyrimidin-4-amine (1.295 g, 10 mmol) in DMF (25 mL) was added sodium hydride (1.2 g, 30 mmol, 60% dispersion in mineral oil) in one portion. The mixture was stirred at 0° C. for 10 min and then 2,6-dichlorobenzoyl chloride (2.304 g, 11 mmol) was added dropwise. The mixture was warmed to room temperature and stirred under nitrogen overnight. The mixture was quenched with ice water and the resulting precipitate was collected by filtration. The solid was washed with water, then 1:1 ether/hexane (10 mL,) to give N-(6-chloropyrimidin-4-yl)-2,6-dichlorobenzamide (1.95 g, yield: 64%). 1H NMR (500 MHz, DMSO) δ 12.09 (s, 1H), 8.84 (s, 1H), 8.24 (s, 1H), 7.61-7.56 (m, 2H), 7.53 (dd, J=9.2, 6.8 Hz, 1H). LCMS (ESI) m/z: 302.1 [M+H+].

後処理

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred under nitrogen overnight
  3. customThe mixture was quenched with ice water
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe solid was washed with water

出典と根拠

ORDレコード
ord-05bf36efbaea41deb25c5c872508cf25
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

反応ノート

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