1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide

HRID 2094452

반응식

HRID 2094452 반응식
[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[OH:22].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:13]=1[OH:22])=[O:6]

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1202462-Amino-4-(trifluoromethyl)phenolHCID 8179723-Bromoisonicotinic acid

생성물 1

HCID 668798803-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide수율 23.7%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

A mixture of 0.69 g of 3-bromo isonicotinic acid, 0.60 g of 2-amino-4-(trifluoromethyl)phenol, 1.00 g of WSC and 6 ml of pyridine was stirred while heating at 80° C. for two hours. The reaction mixture was cooled to room temperature, and then concentrated. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixture solvent of ethyl acetate and hexane to give 0.29 g of 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was washed with a mixture solvent of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-5419cb4747a94e9c8b50a3e4d2d1cc06
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445522B2

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