Dabco → HCID 67958277、化合物

HRID 2369593ノート

反応式

HRID 2369593 の反応式
N12CCN(CC1)CC2.[CH3:9][N:10]([CH3:15])[S:11](Cl)(=[O:13])=[O:12].[CH2:16]([O:18][C:19]([C:21]1[NH:22][N:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)=[O:20])[CH3:17]>CC#N.O>[CH2:16]([O:18][C:19]([C:21]1[N:22]([S:11](=[O:13])(=[O:12])[N:10]([CH3:15])[CH3:9])[N:23]=[C:24]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)=[O:20])[CH3:17]

参加物

6

反応物 3

HCID 9237DabcoHCID 83372Dimethylsulphamoyl chlorideHCID 178469067HCID 178469067、化合物

生成物 1

HCID 67958277HCID 67958277、化合物収率 84.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

1,4-Diazabicylo[2.2.2]octane (1.0 g, 8.93 mmol) and dimethylsulfamoyl chloride (0.88 mL, 8.2 mmol) were sequentially added to a solution of 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (2.0 g, 8.12 mmol) in CH3CN (10 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The mixture was diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents concentrated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 40/60). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (2.42 g, 84% yield) as a white solid.

後処理

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe solvents concentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 40/60)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-e4a98de59dd349cca55479fdc0ce8560
出典データセット
uspto-grants-2014_04
特許番号
US08703946B2

反応ノート

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