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

HRID 884944
ノート
印刷プレビュー

反応式

HRID 884944 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d1122455e5634c0a97f833ef1db452d0
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242133B2

反応ノート

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