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

HRID 2094452

反応式

HRID 2094452 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5419cb4747a94e9c8b50a3e4d2d1cc06
出典データセット
uspto-grants-2013_05
特許番号
US08445522B2

関連ノート

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