Benzene → N-(ethoxymethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250499노트

반응식

HRID 1250499 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[C:5]([C:20]([NH2:22])=[O:21])[CH:4]=1.C1C=CC=CC=1.[H-].[Na+].[CH2:31]([O:33][CH2:34]Cl)[CH3:32]>C(OCC)(=O)C.CN(C=O)C>[CH2:31]([O:33][CH2:34][NH:22][C:20]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[CH:11]=2)[N:6]=1)=[O:21])[CH3:32]

참가 물질

7

반응물 4

HCID 241BenzeneHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 183262294-Methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

생성물 1

HCID 18326199N-(ethoxymethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1.0 g (0.0032 mol) of 4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide was dissolved in a mixed solvent containing about 20 ml of benzene and about 10 ml of DMF, and the obtained solution was mixed with 0.14 g (ca. 60% in mineral oil; 0.0032×1.1 mol) of NaH, followed by treating the solution under reflux for several minutes. Thereafter, the resultant reaction solution was mixed with 0.61 g (0.0032×2.0 mol) of chloromethyl ethyl ether, followed by treating the solution under reflux for about 3 hours. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water and then washed with saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

후처리

  1. additionby treating the solution
  2. temperatureunder reflux for several minutes
  3. customThereafter, the resultant reaction solution
  4. additionby treating the solution
  5. temperatureunder reflux for about 3 hours
  6. washwashed with saturated brine
  7. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-62b2204abffd4f3dad30fcadf711d46e
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339045B1

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