Hydrochloric Acid → 3-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid

HRID 1160444Notes

Reaction equation

HRID 1160444 reaction equation
[CH3:1][N:2]([S:17]([CH3:20])(=[O:19])=[O:18])[C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9].[OH-].[K+].CO.Cl>O1CCCC1>[CH3:16][O:15][C:13]([C:5]1[CH:6]=[C:7]([CH:12]=[C:3]([N:2]([CH3:1])[S:17]([CH3:20])(=[O:19])=[O:18])[CH:4]=1)[C:8]([OH:10])=[O:9])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

Product 1

HCID 111503713-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of dimethyl 5-[methyl(methylsulfonyl)amino]isophthalate obtained in Reference Example 5 36.0 g (119 mmol), potassium hydroxide 8.71 g (155 mmol), methanol (360 mL) and tetrahydrofuran (240 mL) was stirred at 90° C. for 1.5 hours. To a mixture of 1N hydrochloric acid (200 mL) and ice water (500 mL) was added the reaction mixture dropwise, and the precipitated solid was collected by filtering, and dried under vacuum to give 32.4 g (113 mmol) of the title compound (yield: 95%).

Workup

  1. additionwas added the reaction mixture dropwise
  2. customthe precipitated solid was collected
  3. filtrationby filtering
  4. customdried under vacuum

Sources & evidence

ORD record
ord-559e6d83a0814b8bb9791a85a71cff52
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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