Monomethylamine methanol → HCID 68411361, compound

HRID 2194698Notes

Reaction equation

HRID 2194698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[N:12]=[C:11]([C:21]([O:23]CC)=O)[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:26][NH2:27].CO>CO>[Br:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[N:12]=[C:11]([C:21]([NH:27][CH3:26])=[O:23])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57454252Monomethylamine methanolHCID 68412747HCID 68412747, compound

Product 1

HCID 68411361HCID 68411361, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 5-[(3-bromophenyl)thio]-1-(2-chlorophenyl)-1H-pyrazole-3-carboxylate (687 mg) in methanol (8 mL) was added 40% methylamine-methanol solution (1.6 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 to give the title compound as a yellow oil (yield 600 mg, yield 90%).

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

Sources & evidence

ORD record
ord-219646f1666142f6992d812ef3b5fd0b
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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