Monomethylamine methanol → HCID 68409745, compound

HRID 2194699Notes

Reaction equation

HRID 2194699 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[N:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])[N:12]=[C:11]([C:22]([O:24]CC)=O)[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:27][NH2:28].CO>CO>[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[N:13]([C:14]3[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=3[F:21])[N:12]=[C:11]([C:22]([NH:28][CH3:27])=[O:24])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57454252Monomethylamine methanolHCID 68410662HCID 68410662, compound

Product 1

HCID 68409745HCID 68409745, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-[(3-bromophenyl)thio]-1-(2,5-difluorophenyl)-1H-pyrazole-3-carboxylate (2.04 g) in methanol (2 mL) was added 40% methylamine-methanol solution (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hr, and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1) to give the title compound as a yellow oil (yield 1.35 g, yield 76%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ab0d2f297c184045adb5825c61a4bf10
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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