Hydrochloric Acid → HCID 66925264, compound

HRID 554437Notes

Reaction equation

HRID 554437 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH:26]=O)[CH:9]=1.CO.[CH3:30][NH2:31].[BH4-].[Na+].[ClH:34].C(=O)([O-])O.[Na+]>CO>[ClH:34].[CH3:30][NH:31][CH2:26][C:10]1[CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH3:25])(=[O:23])=[O:24])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86620787HCID 86620787, compound

Product 1

HCID 66925264HCID 66925264, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(2-Methylphenyl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde (250 mg) was dissolved in methanol (25 mL), 40% methylamine methanol solution (482 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (71 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (30 mL) was added, and the mixture was stirred for 5 min. The reaction mixture was alkalized with a saturated aqueous sodium hydrogencarbonate solution and 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: ethyl acetate-methanol=1:0→7:3), and dissolved in methanol (5 mL). To the solution was added a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL), and the mixture was concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound as colorless crystals (yield 156 mg, 55%).

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. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=1:0→7:3)
  8. dissolutiondissolved in methanol (5 mL)
  9. additionTo the solution was added a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL)
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5716678fced1423e842357fe59c5ddba
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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