Hydrochloric Acid → HCID 57522145, compound

HRID 554420Notes

Reaction equation

HRID 554420 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([S:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([CH:25]=O)=[CH:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].CO.[CH3:29][NH2:30].[BH4-].[Na+].[ClH:33].C(=O)([O-])O.[Na+]>CO>[ClH:33].[CH3:29][NH:30][CH2:25][C:16]1[CH:17]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]([S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)(=[O:13])=[O:12])[CH:15]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 57522259HCID 57522259, compound

Product 1

HCID 57522145HCID 57522145, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-{[3-(Methylsulfonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrole-3-carbaldehyde (160 mg) was dissolved in methanol (20 mL), 40% methylamine methanol solution (160 mg) was added at room temperature, and the mixture was stirred for 30 min. Sodium borohydride (32 mg) was added at room temperature, and the mixture was stirred for 10 min. 1 mol/L Hydrochloric acid (20 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 dissolved in methanol (5 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added, and the mixture was concentrated under reduced pressure. The residue was crystallized from tetrahydrofuran to give the title compound as colorless crystals (yield 150 mg, 83%).

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. dissolutionThe residue was dissolved in methanol (5 mL)
  8. additiona 4 mol/L hydrogen chloride-ethyl acetate solution (1 mL) was added
  9. concentrationthe mixture was concentrated under reduced pressure
  10. customThe residue was crystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-38d3e2c6c4074ea3ac963ee4d00812ea
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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