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Acetone → 5-azidocarbonyl-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1024317
ノート
印刷プレビュー

反応式

HRID 1024317 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([OH:13])=O)[CH:6]=1)=[O:4].S(Cl)(Cl)=O.CC(C)=O.[N-:22]=[N+:23]=[N-:24].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]([N:22]=[N+:23]=[N-:24])=[O:13])[CH:6]=1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 180AcetoneHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 142660565-(Methoxycarbonyl)-1-Methyl-1H-Pyrazole-3-Carboxylic Acid

生成物 1

HCID 576193625-azidocarbonyl-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

1-Methyl-1H-pyrazole-3,5-dicarboxylic acid 5-methyl ester (641, 3.2 g, 17.0 mmol) was combined with thionyl chloride (5 mL). The reaction was heated to reflux for 40 minutes and then concentrated twice from toluene. The resulting solid was dried under reduced pressure overnight. The product was dissolved into acetone (20 mL) and sodium azide (3.5 g, 54.0 mmol) was added in water (10 mL) rapidly at once. The obtained solution was stirred for one minute and then poured into ice-water (50 mL). The precipitate was filtered and dried under reduced pressure. The final compound was used without further purification (642, 2.8 g, 77%).

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 40 minutes
  3. concentrationconcentrated twice from toluene
  4. customThe resulting solid was dried under reduced pressure overnight
  5. filtrationThe precipitate was filtered
  6. customdried under reduced pressure
  7. customThe final compound was used without further purification (642, 2.8 g, 77%)

出典と根拠

ORDレコード
ord-e60ee4b3280b423cba01d1704d7bfd8b
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722702B2

反応ノート

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