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Acetic Acid → 1-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrile

HRID 839219
ノート
印刷プレビュー

反応式

HRID 839219 の反応式
[N+:1]([C:4]1[O:8][C:7]([C:9]2[C:13]([C:14]#[N:15])=[CH:12][NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].CI.[C:20](O)(=O)C>CN(C)C=O.O>[CH3:20][N:11]1[CH:12]=[C:13]([C:14]#[N:15])[C:9]([C:7]2[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1785104403-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrile

生成物 1

HCID 203260431-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbonitrile収率 57%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6228Dimethylformamide溶媒2 回

実験手順

Add 15.4 g of 3-(5-nitro-2-furyl)-1H-pyrazole-4-carbonitrile portionwise to a suspension of 2.5 g of sodium hydride (80% in liquid paraffin) in 90 ml of dimethylformamide while stirring and under nitrogen at from -2° C to -5° C. Stir the thus-obtained reaction mixture for 30 minutes and then add dropwise thereto a solution of 11.8 g of methyl iodide in 20 ml of dimethylformamide. After stirring for 30 minutes, admix therewith 0.6 g of glacial acetic acid and stir the resulting solution into 220 g of ice and water. Remove formed precipitate by vacuum filtration and recrystallize residue twice from dimethylformamide and water. Dry the residue in vacuo. Recrystallize the resulting 13.5 g of product three more times from dimethylformamide and water to obtain a 57% yield of 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carbonitrile [m.p. 176.5° to 177.5° C].

後処理

  1. stirringStir
  2. customthe thus-obtained reaction mixture for 30 minutes
  3. additionadd dropwise
  4. stirringAfter stirring for 30 minutes
  5. customRemove
  6. customformed precipitate
  7. filtrationby vacuum filtration
  8. customrecrystallize residue twice from dimethylformamide and water
  9. customDry the residue in vacuo
  10. customRecrystallize the resulting 13.5 g of product three more times from dimethylformamide and water

出典と根拠

ORDレコード
ord-f9287ec750a7468bb14e4d5c08189f6d
出典データセット
uspto-grants-1978_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04093812

反応ノート

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