Hydrochloric Acid → 5-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

HRID 1367303

反応式

HRID 1367303 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.N1C=CC=CC=1.Cl>C(#N)C.CN(C)C1C=CN=CC=1.O>[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)=[O:9])=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 78124-ChloroanilineHCID 190907715-Bromo-pyridine-2-carbonyl chloride

生成物 1

HCID 595933715-Bromo-pyridine-2-carboxylic acid (4-chloro-phenyl)-amide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
68 °C

実験手順

To 5-Bromo-pyridine-2-carbonyl chloride (69, 0.76 g, 3.4 mmol) in acetonitrile (29.0 mL) were added p-chloroaniline (53, 0.702 g, 5.50 mmol), 4-dimethylamino-pyridine (0.12 g, 0.96 mmol) and pyridine (2.9 mL, 0.036 mol). The reaction was stirred at 68° C. overnight, then poured into water, acidified with 1 N HCl to pH around 1 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with dichloromethane to give a white solid (70, 0.75 g, 70.0%).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with dichloromethane
  7. customto give a white solid (70, 0.75 g, 70.0%)

出典と根拠

ORDレコード
ord-83050277b98a4112835c0748094cfce5
出典データセット
uspto-grants-2011_02
特許番号
US07893075B2

関連ノート

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