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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 533600
ノート
印刷プレビュー

反応式

HRID 533600 の反応式
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[CH2:14]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=O)[CH:15]=[CH2:16].CCN=C=NCCCN(C)C>C1(C)C(C)=CC=CC=1>[CH2:14]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]2[N:9]=1)[CH:15]=[CH2:16]
参加物反応条件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 2646962-Allylsulfanylbenzoic acidHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamine

生成物 1

HCID 867081952-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine収率 47.3%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
145 °C

実験手順

A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-allylsulfanylbenzoic acid (1.46 g), WSC (1.06 g), and xylene (10 ml) was stirred with heating at 145° C. for 3 hours. After the mixture was evaporated to remove xylene, acetic acid (10 ml) was added thereto, and stirred with heating at 120° C. for further 1 hour. To the reaction mixture cooled to room temperature, 5 mol/l of aqueous sodium hydroxide solution was added to neutralize, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.83 g of 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 10).

後処理

  1. customAfter the mixture was evaporated
  2. customto remove xylene, acetic acid (10 ml)
  3. additionwas added
  4. stirringstirred
  5. temperaturewith heating at 120° C. for further 1 hour
  6. temperatureTo the reaction mixture cooled to room temperature
  7. addition5 mol/l of aqueous sodium hydroxide solution was added
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1beabfb146994d988cb9668b57920613
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853238B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート