Potassium Carbonate → 4-(4-chlorobenzylthio)pyridin-2(1H)-one

HRID 1044405

反応式

HRID 1044405 の反応式
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][SH:23])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][S:23][C:2]2[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=2)=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 804094-Chlorobenzyl mercaptanHCID 27576114-Chloropyridin-2-ol

生成物 1

HCID 585802484-(4-chlorobenzylthio)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-chloropyridin-2(1H)-one (100 mg, 0.77 mmol), K2CO3 (320 mg, 2.32 mmol) and (4-chlorophenyl)methanethiol (612 mg, 3.86 mmol) was stirred at 100° C. for 18 hours. After cooling the reaction to RT and was dilution with CH2Cl2 (5 mL), the crude product was subjected to flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient, employing LC-MS to identify the fractions containing the desired product) to afford 4-(4-chlorobenzylthio)pyridin-2(1H)-one 8A (96 mg, 46.9% yield). 1H NMR (400 MHz, Chloroform-D) δ ppm 12.30 (1H, br. s.), 7.28-7.43 (4H, m), 7.15 (1H, d, J=7.03 Hz), 6.28 (1H, d, J=1.51 Hz), 6.11 (1H, dd, J=6.90, 1.88 Hz), 4.11 (2H, s).

後処理

  1. temperatureAfter cooling
  2. customthe reaction to RT

出典と根拠

ORDレコード
ord-eaece1f5915746189f97693d48383c3f
出典データセット
uspto-grants-2013_10
特許番号
US08563583B2

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