Methanol → Methyl 2-hydroxy-5-sulfamoylbenzoate

HRID 1820822Notes

Reaction equation

HRID 1820822 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15]1N=CN(C(N2C=NC=C2)=O)C=1.CO>C1COCC1>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:9]=[CH:10][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 77312702-Hydroxy-5-sulfamoylbenzoic acid

Product 1

HCID 14266941Methyl 2-hydroxy-5-sulfamoylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 62 mmol 2-hydroxy-5-sulfamoyl-benzoic acid in 80 ml THF was added 80 mmol CDI and the mixture heated at 50° C. for 1 h. 616 mmol methanol was then added, and the mixture was heated at 50° C. for 16 h. The mixture was then cooled to room temperature, concentrated in vacuo, and the residue chromatographed on silica gel (eluant: dichloromethane/methanol 20:1). The product containing fractions were concentrated in vacuo and the residue suspended in ethyl acetate and washed with aq NaHCO3 solution. The organic phase was dried with Na2SO4 and concentrated in vacuo to afford the title compound. MS (m/e): 230.2 ([M−H]−, 100%)

Workup

  1. temperaturethe mixture was heated at 50° C. for 16 h
  2. temperatureThe mixture was then cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customthe residue chromatographed on silica gel (eluant: dichloromethane/methanol 20:1)
  5. additionThe product containing fractions
  6. concentrationwere concentrated in vacuo
  7. washwashed with aq NaHCO3 solution
  8. dry with materialThe organic phase was dried with Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60b045a39ba14cd9aa06ad504ff2a7d7
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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