Methanol → 2-Fluoro-5-(propane-1-sulfonylamino)-benzoic acid methyl ester

HRID 250719Notes

Reaction equation

HRID 250719 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:23]O>>[CH3:23][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[CH:9]=[CH:10][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 580866942-Fluoro-5-(propylsulfonamido)benzoic acid

Product 1

HCID 595068652-Fluoro-5-(propane-1-sulfonylamino)-benzoic acid methyl ester

Procedure

To 2-Fluoro-5-(propane-1-sulfonylamino)-benzoic acid (669, 2.0 g, 0.0076 mol) in methanol (20.0 mL) was added sulfuric acid (0.90 mL, 0.017 mol). The reaction was stirred at room temperature overnight. The reaction was concentrated and purified with silica gel column chromatograph eluting with 20% ethyl acetate in hexane to give a white solid (670, 1.27 g, 62%). MS (ESI) [M−H+]−=274.1.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified with silica gel column chromatograph
  3. washeluting with 20% ethyl acetate in hexane
  4. customto give a white solid (670, 1.27 g, 62%)

Sources & evidence

ORD record
ord-58265d9cab1e4100aa0f52beb1c99800
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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