3-[(3-Chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamide → 3-[1-(3-Chloro-phenyl)-1-(2-methyl-propane-2-sulfinylamino)-ethyl]-pyrazole-1-sulfonic acid dimethylamide

HRID 1912465ノート

反応式

HRID 1912465 の反応式
[CH3:1][Mg]Br.[CH3:4][N:5]([CH3:29])[S:6]([N:9]1[CH:13]=[CH:12][C:11]([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[N:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17])=[N:10]1)(=[O:8])=[O:7]>C1COCC1>[CH3:29][N:5]([CH3:4])[S:6]([N:9]1[CH:13]=[CH:12][C:11]([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)([NH:15][S:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[O:17])[CH3:1])=[N:10]1)(=[O:8])=[O:7]

参加物

4

反応物 2

HCID 866908083-[(3-Chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 668253223-[1-(3-Chloro-phenyl)-1-(2-methyl-propane-2-sulfinylamino)-ethyl]-pyrazole-1-sulfonic acid dimethylamide収率 99.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Methylmagnesium bromide (15.08 mL, 21.11 mmol) was added to a solution of 3-[(3-chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamide (2.2 g, 5.28 mmol) in THF (25 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 2 hours, quenched with NH4Cl (aq. sat. solution) and the product was extracted with DCM. 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 100/0). The desired fractions were collected and concentrated in vacuo to yield 3-[1-(3-chloro-phenyl)-1-(2-methyl-propane-2-sulfinylamino)-ethyl]-pyrazole-1-sulfonic acid dimethylamide (2.28 g, 99% yield) as a colourless oil which solidified upon standing.

後処理

  1. customquenched with NH4Cl (aq. sat. solution)
  2. extractionthe product was extracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 100/0)
  8. customThe desired fractions were collected
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d9c49922e7804c35aa9daa52eccb3fa4
出典データセット
uspto-grants-2013_12
特許番号
US08609660B2

反応ノート

読み込み中…