Hydrochloric Acid → 2-Methoxy-5-methylsulfonamidobenzoic Acid

HRID 637193Notes

Reaction equation

HRID 637193 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Li+].Cl>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 12848748HCID 12848748, compound

Product 1

HCID 128487462-Methoxy-5-methylsulfonamidobenzoic Acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Combine methyl 2-methoxy-5-methylsulfonamidobenzoate (1.0 g, 3.86 mmol) and lithium hydroxide (93 mg, 3.86 mmol) in tetrahydrofuran/water (50 mL/10 mL). After 18 hours, add lithium hydroxide (100 mg) and heat to reflux. After 1 hour, cool to ambient temperature and evaporate to remove most of the tetrahydrofuran. Dilute the evaporated reaction mixture with water (about 70 mL) and acidify to pH of about 1 using a 1 M aqueous hydrochloric acid solution. Evaporate to dryness and triturate with dichloromethane (200 mL). Filter and evaporate the filtrate to give the title compound: mp; 160-163° C.

Workup

  1. temperatureheat to reflux
  2. waitAfter 1 hour
  3. customevaporate
  4. customto remove most of the tetrahydrofuran
  5. additionDilute
  6. customthe evaporated reaction mixture with water (about 70 mL)
  7. customEvaporate to dryness
  8. customtriturate with dichloromethane (200 mL)
  9. filtrationFilter
  10. customevaporate the filtrate

Sources & evidence

ORD record
ord-73786a0e8ca1432ca8f0ee2cf7bb7f07
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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