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

HRID 1024190

반응식

HRID 1024190 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
68 °C

실험 절차

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 1N 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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-8d55364b25e644b4a76c53b27d8e02a8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722702B2

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