Sodium hydride → HCID 45790144、化合物

HRID 1912461ノート

反応式

HRID 1912461 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:6].[CH3:12][N:13]([CH3:18])[S:14](Cl)(=[O:16])=[O:15]>C1COCC1.O>[CH3:3][O:4][C:5]([C:7]1[CH:11]=[CH:10][N:9]([S:14](=[O:16])(=[O:15])[N:13]([CH3:18])[CH3:12])[N:8]=1)=[O:6]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 83372Dimethylsulphamoyl chlorideHCID 178498454HCID 178498454、化合物

生成物 1

HCID 45790144HCID 45790144、化合物収率 75.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Sodium hydride (1.57 g, 41.03 mmol) was added to a solution of 1H-pyrazole-3-carboxylic acid methyl ester (3.45 g, 27.36 mmol) in THF (20 mL) at 0° C. The mixture was stirred at 0° C. for 30 minutes. Then dimethylsulfamoyl chloride (4.41 mL, 41.03 mmol) was added and the mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was diluted with water and the product extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and concentrated in vacuo to yield 1-dimethylsulfamoyl-1H-pyrazole-3-carboxylic acid methyl ester (4.8 g, 75% yield) as a colourless oil.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 18 hours
  3. extractionthe product extracted with AcOEt
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90)
  9. customThe desired fractions were collected
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-22e3623466c042f28356acbf719adcef
出典データセット
uspto-grants-2013_12
特許番号
US08609660B2

反応ノート

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