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 1912465Notes

Reaction equation

HRID 1912465 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d9c49922e7804c35aa9daa52eccb3fa4
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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