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

HRID 1250507노트

반응식

HRID 1250507 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]([OH:22])=O)[CH:4]=1.S(Cl)(Cl)=O.C1C=CC=CC=1.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>C(OCC)(=O)C.CN(C=O)C>[CH2:33]([N:35]([CH2:36][CH3:37])[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:17])([F:18])[F:19])[CH:11]=2)[N:6]=1)=[O:22])[CH3:34]

참가 물질

7

반응물 4

HCID 241BenzeneHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 109030764-Methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid

생성물 1

HCID 18326212N,N-diethyl-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

0.40 g (0.00128 mol) of 4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxylic acid was mixed with 0.3 g (0.00128×2.0 mol) of thionyl chloride and then with about 10 ml of benzene and a small amount of DMF, followed by treating the obtained mixture under reflux for about 30 minutes. The reaction solution was concentrated and mixed with methylene chloride and then with 0.23 g (0.00128×2.5 mol) of diethyl amine, followed by stirring at room temperature for about one hour. The reaction solution was distributed in ethyl acetate-saturated sodium bicarbonate water, and 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 obtained mixture
  2. temperatureunder reflux for about 30 minutes
  3. concentrationThe reaction solution was concentrated
  4. additionmixed with methylene chloride
  5. washwashed with saturated brine
  6. dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ce24d79fe0b9466c89b20836bde1deaf
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06339045B1

반응 노트

불러오는 중…