Hydrogen chloride-ethyl acetate → Methyl 2-({4-[(methylamino)methyl]-2-phenyl-1H-pyrrol-1-yl}sulfonyl)benzoate hydrochloride

HRID 554422Notes

Reaction equation

HRID 554422 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]([S:9]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])(=[O:11])=[O:10])[CH:8]=1.C(OCC)(=O)C.[ClH:34]>C(OCC)(=O)C>[ClH:34].[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]([S:9]([C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])(=[O:10])=[O:11])[CH:8]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66925025methyl 2-({4-[(methylamino)methyl]-2-phenyl-1H-pyrrol-1-yl}sulfonyl)benzoate

Product 1

HCID 66925109Methyl 2-({4-[(methylamino)methyl]-2-phenyl-1H-pyrrol-1-yl}sulfonyl)benzoate hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution (1 mL) of methyl 2-({4-[(methylamino)methyl]-2-phenyl-1H-pyrrol-1-yl}sulfonyl)benzoate (105 mg) in ethyl acetate was added 4 mol/L hydrogen chloride-ethyl acetate solution (0.5 mL) at room temperature. The solvent was evaporated under reduced pressure, and the residue was crystallized from 2-propanol and isopropyl ether. The obtained crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol to give the title compound as colorless crystals (yield 68 mg, 60%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was crystallized from 2-propanol and isopropyl ether
  3. customThe obtained crystals were recrystallized from a mixed solvent of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-ebe8500fc7e04a4c8c266b54cc23b1a7
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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