Ammonium Chloride → HCID 67182399, compound

HRID 2425554Notes

Reaction equation

HRID 2425554 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1/[CH:8]=[N:9]/[S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11].[CH3:16][Mg]Br.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C@H:8]([NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH3:16]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 87300988HCID 87300988, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67182399HCID 67182399, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(S,E)-N-((5-chloro-1-methyl-1H-pyrazol-4-yl)methylene)-2-methylpropane-2-sulfinamide(750 mg, 3.03 mmol) was dissolved in THF (25 ml) placed under nitrogen and cooled to −78° C. 1.4M methyl magnesium bromide solution (toluene:THF 3:1, 8.65 ml, 12.1 mmol) was added dropwise and reaction stirred overnight while warming to room temperature. Saturated aqueous ammonium chloride solution (20 ml) was added to the reaction and stirred for 5 minutes. The product was extracted with EtOAc (2×15 ml), combined organics were washed with brine (15 ml), dried over Na2SO4, filtered and concentrated to furnish the title product as a brown gum (690 mg, 86.4% yield). 1H NMR (400 MHz, CDCl3) 1.18-1.19 (9H s) 1.55-1.57 (3H d) 1.62-1.64 (3H s) 3.20-3.22 (1H d) 4.41-4.47 (1H q) 7.42 (1H s) MS (ESI) m/z 264 (M+H)+

Workup

  1. customreaction
  2. temperaturewhile warming to room temperature
  3. stirringstirred for 5 minutes
  4. extractionThe product was extracted with EtOAc (2×15 ml)
  5. washcombined organics were washed with brine (15 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-62fe6bdaabc44a8ba3793b29bc06e955
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

Loading…