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

HRID 1912464Notes

Reaction equation

HRID 1912464 reaction equation
[CH3:1][N:2]([CH3:20])[S:3]([N:6]1[CH:10]=[CH:9][C:8]([C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[N:7]1)(=[O:5])=[O:4].[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23]>C1(C)C=CC=CC=1.[Cl-].[Na+].O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][N:2]([CH3:20])[S:3]([N:6]1[CH:10]=[CH:9][C:8]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[N:27][S:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])=[N:7]1)(=[O:5])=[O:4]

Participants

6

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 668264453-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide

Product 1

HCID 866908083-[(3-Chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamideYield 97.3%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

Titanium(IV)isopropoxide (3.22 mL, 10.71 mmol) was added to a mixture of 3-(3-chloro-benzoyl)-1H-pyrazole-1-sulfonic acid dimethylamide (1.68 g, 5.35 mmol) and 2-methyl-2-propanesulfinamide (0.71 g, 5.89 mmol) in toluene (32 mL) under nitrogen. The mixture was stirred at 110° C. for 24 hours. The mixture was cooled and poured into brine while rapidly stirring. The mixture was filtered through diatomaceous earth and the filter cake was washed with AcOEt. The filtrate was transferred to a separation funnel where 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 3-[(3-chloro-phenyl)-(2-methyl-propane-2-sulfinylimino)-methyl]-pyrazole-1-sulfonic acid dimethylamide (2.17 g, 97% yield) as a yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. stirringwhile rapidly stirring
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. washthe filter cake was washed with AcOEt
  5. customThe filtrate was transferred to a separation funnel
  6. customwhere the organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvents evaporated in vacuo
  10. customThe crude product was purified by flash column chromatography (silica gel; AcOEt in DCM 0/100 to 10/90)
  11. customThe desired fractions were collected
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb00270fae33410fa5888d2354612190
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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