Hydrochloric Acid → 5-(Methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid

HRID 732515Notes

Reaction equation

HRID 732515 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:16]=[C:15]([N:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH3:18])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.[OH-].[Na+].Cl>C1COCC1.C(OCC)(=O)C>[CH3:22][S:19]([N:17]([CH3:18])[C:15]1[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=[C:4]([CH:16]=1)[C:3]([OH:23])=[O:2])(=[O:21])=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688153705-(Methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 210620595-(Methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-(methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid methyl ester (1.09 g, 3.18 mmol) in THF (80 mL) and add 1 N NaOH (16 mL, 16 mmol). Stir at room temperature for 16 h and add 5 N HCl (5 mL). Dilute with ethyl acetate, wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound.

Workup

  1. washwash with saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-8d608b70d72c44ad8a1222ef622042bb
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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