Sodium hydride → HCID 86648969, 화합물

HRID 449936노트

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HRID 449936 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86648969HCID 86648969, 화합물수율 64.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-05bf36efbaea41deb25c5c872508cf25
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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