Methanol → 2-Hydroxy-5-methylsulfamoyl-benzoic acid methyl ester

HRID 1930987Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](=[O:15])(=[O:14])[NH:12][CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:16]1N=CN(C(N2C=NC=C2)=O)C=1.CO>C1COCC1>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([S:11](=[O:15])(=[O:14])[NH:12][CH3:13])[CH:9]=[CH:10][C:2]=1[OH:1]

Participants

Conditions

Temperature: 70 °C

Procedure

To 77 mmol 2-hydroxy-5-methylsulfamoyl-benzoic acid in 300 ml THF was added 85 mmol CDI and the mixture heated at 70° C. for 1 h. 770 mmol methanol was then added and the mixture was heated at 70° C. for 16 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane/dichloromethane 45:45:10) to afford the title compound. MS (m/e): 244.1 ([M−H]−, 100%)

Workup

temperaturethe mixture was heated at 70° C. for 16 h
temperatureThe mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane/dichloromethane 45:45:10)

Sources & evidence

ORD record: ord-d37d3349d92a4cad806a144980cff62a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188139B2

Reaction notes

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