Hydrochloric Acid → HCID 66924794, compound

HRID 554391Notes

Reaction equation

HRID 554391 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][C:13]([CH:22]=O)=[CH:12]1)(=[O:10])=[O:9].CO.[CH3:26][NH2:27].[BH4-].[Na+].[ClH:30].C(=O)([O-])O.[Na+]>CO>[ClH:30].[CH3:26][NH:27][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:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])(=[O:10])=[O:9])[CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86232940HCID 86232940, compound

Product 1

HCID 66924794HCID 66924794, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[(2-Methylphenyl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde (390 mg) was dissolved in methanol (10 mL), 40% methylamine methanol solution (280 mg) was added at room temperature and the mixture was stirred for 15 min. To the reaction mixture was added sodium borohydride (70 mg) at room temperature and the mixture was stirred for 10 min. Thereto was added 1 mol/l hydrochloric acid (10 mL), and the mixture was stirred for 5 min. The mixture was alkalized with a saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=50:50→0:100), and the obtained oil was dissolved in ethyl acetate (5 mL). 4 mol/l Hydrochloric acid-ethyl acetate (1 mL) was added and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 342 mg, 76%).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe mixture was stirred for 5 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=50:50→0:100)
  8. dissolutionthe obtained oil was dissolved in ethyl acetate (5 mL)
  9. addition4 mol/l Hydrochloric acid-ethyl acetate (1 mL) was added
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-146ee4d6ae3e4e24b9b37c6c51e21783
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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