Sodium Hydroxide → HCID 68670358, compound

HRID 2071059Notes

Reaction equation

HRID 2071059 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:8]=[C:9]([C:18]([O:20][CH2:21]C)=[O:19])[CH:10]=[C:11]([CH:17]=1)[C:12]([O:14]CC)=[O:13])(=[O:4])=[O:3].[OH-].[Na+]>C1COCC1.CO.O>[CH3:21][O:20][C:18]([C:9]1[CH:10]=[C:11]([CH:17]=[C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=1)[C:12]([OH:14])=[O:13])=[O:19]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68670050HCID 68670050, compound

Product 1

HCID 68670358HCID 68670358, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 901 mg (2.73 mmol) of diethyl 5-(methylsulfonamidomethyl)isophthalate in 10 mL of THF and 10 mL of MeOH was added 115 mg of NaOH in 2.7 mL of H2O. After the solution was stirred at r.t. for 50 h, the solution was concentrated, and H2O and CHCl3 were added. The aqueous layer was acidified to pH=1-2 with 1N HCl and extracted with the extract of (40 mL of CHCl3: 5 mL of MeOH, and 5 mL of H2O) several times. The combined extracts were dried over Na2SO4, filtered, and concentrated to give crude 3-(methoxycarbonyl)-5-(methylsulfonamidomethyl)benzoic acid which was used without further purification.

Workup

  1. concentrationthe solution was concentrated
  2. additionH2O and CHCl3 were added
  3. extractionextracted with the
  4. extractionextract of (40 mL of CHCl3: 5 mL of MeOH, and 5 mL of H2O) several times
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-99e0b306909d49f6b24b07d54b32e29b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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