Methanamine, hydrochloride (1:1) → HCID 66561648, compound

HRID 554384Notes

Reaction equation

HRID 554384 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)=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].C[NH3+].[C:27]([BH3-])#[N:28].[Na+].C(=O)([O-])O.[Na+]>CO>[CH3:27][NH:28][CH2:22][C:13]1[CH:14]=[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])[CH:12]=1

Participants

6

Reactant 4

HCID 11637Methanamine, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 86232905HCID 86232905, compound

Product 1

HCID 66561648HCID 66561648, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (10 mL) of 1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (200 mg) in methanol were added methylammonium chloride (207 mg) and sodium cyanoborohydride (39 mg), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, 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=6:1→1:1) to give the title compound as a brown oil (yield 15 mg, 7%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→1:1)

Sources & evidence

ORD record
ord-607e5e22cb4a46f0bf86b6d002b8a4be
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…