Methanamine, hydrochloride (1:1) → HCID 67004007, compound

HRID 2359962Notes

Reaction equation

HRID 2359962 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH:22]=O)=[N:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-:24].[CH3:25][NH3+:26].[BH4-].[Na+]>CO>[ClH:24].[CH3:25][NH:26][CH2:22][C:13]1[CH:14]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[N:12]=1

Participants

5

Reactant 3

HCID 11637Methanamine, hydrochloride (1:1)HCID 4311764Sodium borohydrideHCID 57687728HCID 57687728, compound

Product 1

HCID 67004007HCID 67004007, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrazole-3-carbaldehyde (220 mg) and methylammonium chloride (455 mg) in methanol (5 mL) was added sodium borohydride (127 mg), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, 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 brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→0:1). The obtained colorless oil was dissolved in ethyl acetate (5 mL), 4 mol/L hydrogen chloride-ethyl acetate solution (0.5 mL) was added, and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as a colorless solid (yield 70 mg, 27%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→0:1)
  8. dissolutionThe obtained colorless oil was dissolved in ethyl acetate (5 mL)
  9. addition4 mol/L hydrogen chloride-ethyl acetate solution (0.5 mL) was added
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-4df6cf76937340f19be84eef5fdb0b22
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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