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

HRID 884944
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HRID 884944 반응식
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:21]=[N:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=O.[NH2:22][C:23]1[CH:28]=[C:27]([C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:24]=1[OH:36]>N1C=CC=CC=1>[Cl:12][C:13]1[CH:21]=[N:20][CH:19]=[CH:18][C:14]=1[C:15]([NH:22][C:23]1[CH:28]=[C:27]([C:29]([F:34])([F:35])[C:30]([F:31])([F:32])[F:33])[CH:26]=[CH:25][C:24]=1[OH:36])=[O:17]
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참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27358163-Chloropyridine-4-carboxylic acidHCID 866510632-Amino-4-(pentafluoroethyl)phenol

생성물 1

HCID 866510493-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide수율 34.4%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of 0.44 g of WSC and 4 ml of pyridine, 0.36 g of 3-chloroisonicotinic acid was added. The reaction mixture was stirred at room temperature for 15 minutes. To the reaction mixture, 0.45 g of 2-amino-4-(pentafluoroethyl)phenol was added and stirred while heating at 60° C. for two hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.25 g of 3-chloro-N-[2-hydroxy-5-(pentafluoroethyl)phenyl]isonicotinamide.

후처리

  1. additionwas added
  2. stirringstirred
  3. temperaturewhile heating at 60° C. for two hours
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionfollowed by extraction with ethyl acetate twice
  8. washThe combined organic layers were washed with water
  9. dry with materiala saturated sodium chloride solution, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d1122455e5634c0a97f833ef1db452d0
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242133B2

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