Methanol → HCID 69036806, compound

HRID 1820794Notes

Reaction equation

HRID 1820794 reaction equation
[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH:15]=2)[C:12]([OH:14])=[O:13])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:17](Cl)(=O)C(Cl)=O.CO.N1C=CC=CC=1>ClC(Cl)C.CN(C=O)C>[CH3:17][O:13][C:12](=[O:14])[C:11]1[CH:15]=[C:7]([S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])[CH:8]=[CH:9][C:10]=1[OH:16]

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 69038734HCID 69038734, compound

Product 1

HCID 69036806HCID 69036806, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneCatalystHCID 6228DimethylformamideSolvent

Procedure

To 7.2 mmol 5-cyclopropanesulfonyl-2-hydroxy-benzoic acid in 20 ml dichloroethane containing a few drops of DMF was added dropwise 8.7 mmol oxalyl chloride. After stirring for 90 min at RT, the reaction mixture was cooled to 0° C. and then 144 mmol methanol was added, followed by 72 mmol pyridine, and stirring continued at RT for 1 h. The mixture was then washed with 1 M aq HCl, dried with Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane gradient) to afford the title compound. MS (m/e): 255.2 ([M−H]−, 100%)

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. stirringstirring
  3. waitcontinued at RT for 1 h
  4. washThe mixture was then washed with 1 M aq HCl
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-af4307c5c40f4aa79536325b6eb43d55
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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