HCID 20188328, compound → (+/-)-1-[2-Hydroxy-2-[4-((methylsulfonyl)amino)phenyl]ethyl]-3-methyl-1H-imidazolium chloride

HRID 65254Notes

Reaction equation

HRID 65254 reaction equation
[ClH:1].[N+](C1C=CC(CCC[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=CC=1)([O-])=O.[Cl-].[CH3:21][S:22]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[O:39])[CH2:33]C2[NH2+]C=CN=2)=[CH:28][CH:27]=1)(=[O:24])=[O:23]>O.[Pd]>[Cl-:1].[OH:39][CH:32]([C:29]1[CH:28]=[CH:27][C:26]([NH:25][S:22]([CH3:21])(=[O:23])=[O:24])=[CH:31][CH:30]=1)[CH2:33][NH+:17]1[CH:18]=[CH:19][N:15]([CH3:14])[CH2:16]1

Participants

5

Reactant 2

HCID 20188328HCID 20188328, compoundHCID 86741032HCID 86741032, compound

Product 1

HCID 20188316(+/-)-1-[2-Hydroxy-2-[4-((methylsulfonyl)amino)phenyl]ethyl]-3-methyl-1H-imidazolium chloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 152.3 g (0.463 mole) of 3-methyl-1[2-[4-((methylsulfonyl)amino)phenyl-2-oxoethyl]-1H-imidazolium chloride in 1 L of distilled water and 7.62 g 10% Pd/C catalyst are placed in a 2 L Parr bottle and hydrogenated at 50 psi pressure for ca. 5 hours. Additional H2 is added as needed to maintain 50 psi pressure. The reaction mixture is filtered and the solvent is evaporated by azeotroping with ethanol to provide the title compound, which may be recrystallized from aqueous ethanol.

Workup

  1. additionAdditional H2 is added
  2. temperatureto maintain 50 psi pressure
  3. filtrationThe reaction mixture is filtered
  4. customthe solvent is evaporated
  5. customby azeotroping with ethanol

Sources & evidence

ORD record
ord-06859232194a438e81b6a8cfaddc161c
Source dataset
uspto-grants-1986_09
Patent number
US04613609

Reaction notes

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