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

HRID 1965020Notes

Reaction equation

HRID 1965020 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-c4a250ad1fea4400bf34cd79a1a9b925
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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