Hydrogen chloride-ethyl acetate → N-methyl-1-[1-(phenylsulfonyl)-5-(3-thienyl)-1H-pyrrol-3-yl]methanamine hydrochloride

HRID 554399Notes

Reaction equation

HRID 554399 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[N:13]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:12]=1)C(=O)OC(C)(C)C.C(OCC)(=O)C.[ClH:36]>CO>[ClH:36].[CH3:1][NH:2][CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[N:13]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[CH:12]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66924935tert-Butyl methyl{[1-(phenylsulfonyl)-5-(3-thienyl)-1H-pyrrol-3-yl]methyl}carbamate

Product 1

HCID 66924888N-methyl-1-[1-(phenylsulfonyl)-5-(3-thienyl)-1H-pyrrol-3-yl]methanamine hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl methyl{[1-(phenylsulfonyl)-5-(3-thienyl)-1H-pyrrol-3-yl]methyl}carbamate (0.62 g) in methanol (10 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (6 mL), and the mixture was stirred at room temperature for 3 hr. Activated carbon was added to the reaction mixture, the mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as a colorless solid (yield 0.38 g, 71%).

Workup

  1. additionActivated carbon was added to the reaction mixture
  2. filtrationthe mixture was filtrated
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-7295a73cbe6b48f79cb613a33381a198
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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