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

HRID 1098536Notes

Reaction equation

HRID 1098536 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-1cfa4268cc1248e2b353c4738c6a1517
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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