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 1912465노트

반응식

HRID 1912465 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d9c49922e7804c35aa9daa52eccb3fa4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609660B2

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