Methanol → 2-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester

HRID 1964892Notes

Reaction equation

HRID 1964892 reaction equation
[F:1][C:2]1[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:18](Cl)(=O)C(Cl)=O.CO>C(Cl)Cl.CN(C)C=O>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:2]=1[F:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 580865772-Fluoro-3-(propylsulfonamido)benzoic acid

Product 1

HCID 579632422-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl esterYield 75.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid (50, 5.05 g, 0.0193 mol) in methylene chloride (100 mL) was added N,N-dimethylformamide (0.075 mL, 0.97 mmol) under an atmosphere of nitrogen. The reaction was cooled with ice/water, followed by slow addition of Oxalyl chloride (2.00 M of in methylene chloride, 10.8 mL, 21.6 mmol). The reaction mixture was stirred at room temperature for 3.0 hours. The reaction was cooled with ice/water, followed by addition of methanol (36.0 mL, 0.89 mol) slowly. The reaction was stirred at room temperature overnight. The reaction was concentrate and purified with silica gel column chromatography eluting with 30% ethyl acetate in hexane to give a crude white solid 4.0 g.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. concentrationThe reaction was concentrate
  3. custompurified with silica gel column chromatography
  4. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1935f0e077b94944bcc4d3fe7e66b7b9
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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