4-Toluenesulfonyl chloride → 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 2198198

反応式

HRID 2198198 の反応式
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[H-].[Na+].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C1COCC1.[NH4+].[Cl-]>[CH2:9]([O:8][C:6]([C:4]1[CH:5]=[N:1][N:2]([S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:3]=1)=[O:7])[CH3:10]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 142179ethyl 1H-pyrazole-4-carboxylate

生成物 1

HCID 216282771-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of ethyl 1H-pyrazole-4-carboxylate (4.50 g, 32.11 mmol) in THF was added 60% NaH (1.60 g, 40.00 mmol) in mineral oil. After 20 minutes, p-toluenesulfonyl chloride was added. After 3 hours, the mixture was diluted with saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 30-50% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford 1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid ethyl ester.

後処理

  1. waitAfter 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 30-50% ethyl acetate in heptane
  8. concentrationthe solvent was concentrated in vacuo

出典と根拠

ORDレコード
ord-3af0b04baf5c473abdec3ebe279e1272
出典データセット
uspto-grants-2012_12
特許番号
US08338610B2

関連ノート

読み込み中…