Chloroform → ethyl 1-(4-bromophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate

HRID 8057

反応式

HRID 8057 の反応式
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14](=[O:22])[CH:15]([C:19](=O)[CH3:20])[C:16](=O)[CH3:17])[CH3:12].C(Cl)(Cl)Cl>C(O)C.N1C=CC=CC=1>[CH2:11]([O:13][C:14]([C:15]1[C:16]([CH3:17])=[N:10][N:9]([C:6]2[CH:7]=[CH:8][C:3]([Br:2])=[CH:4][CH:5]=2)[C:19]=1[CH3:20])=[O:22])[CH3:12]

参加物

6

反応物 3

HCID 6212ChloroformHCID 121574-Bromophenylhydrazine hydrochlorideHCID 79063Ethyl 2-acetylacetoacetate

生成物 1

HCID 9966976ethyl 1-(4-bromophenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1049Pyridine溶媒

実験手順

p-Bromophenylhydrazine hydrochloride (10 mmol, 2.5 g) was added to 2-acetyl-3-oxo-butyric acid ethyl ester (10 mmol, 1.7 g) in ethanol (10 mL) and pyridine (10 mL). The mixture was stirred overnight at room temperature. Thin layer chromatographic (TLC) analysis using chloroform indicated the reaction was complete. The solvents were removed under vacuum. The residue was dissolved in 150 mL ether, then washed with 50 mL water to remove the pyridine. The ether was dried over sodium sulfate (NaSO4), the solids filtered, then the solvents were removed under vacuum. The resulting oil was purified on a silica column. The named product crystallized upon standing in the column effluent, m.p. 71° C.–73° C. Analysis by 1H-NMR and 13C-NMR verified synthesis the named product.

後処理

  1. customThe solvents were removed under vacuum
  2. dissolutionThe residue was dissolved in 150 mL ether
  3. washwashed with 50 mL water
  4. customto remove the pyridine
  5. dry with materialThe ether was dried over sodium sulfate (NaSO4)
  6. filtrationthe solids filtered
  7. customthe solvents were removed under vacuum
  8. customThe resulting oil was purified on a silica column
  9. customThe named product crystallized
  10. customsynthesis the named product

出典と根拠

ORDレコード
ord-e5691291fb0a4b04b21a9e9c660b0e4b
出典データセット
uspto-grants-2006_08
特許番号
US07087634B2

関連ノート

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