Methanol → Methyl 2-chloro-4-(methylsulfonamido)benzoate

HRID 2393009Notes

Reaction equation

HRID 2393009 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:21]O>>[Cl:6][C:7]1[CH:15]=[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:21])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 183504972-Chloro-4-methanesulfonamidobenzoic acid

Product 1

HCID 54238017Methyl 2-chloro-4-(methylsulfonamido)benzoate

Procedure

Concentrated sulphuric acid (20 ml) was added to a suspension of 2-chloro-4-(N-methylsulphonylamino)benzoic acid (10.3 g) in methanol and the mixture was stirred and heated at reflux for 22 hours. It was cooled, evaporated to dryness and diluted with water, extracted with ethyl acetate, washed with aqueous sodium bicarbonate solution, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 2-chloro-4(N-methylsulphonylamino)benzoate(10.0 g) as an off-white solid, NMR (DMSO-d6) 3.15(s,3H) 3.85(s,3H) 7.2(d,1H) 7.3(s,1H) 7.85(d,1H) 10.5(s,1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 22 hours
  3. temperatureIt was cooled
  4. customevaporated to dryness
  5. additiondiluted with water
  6. extractionextracted with ethyl acetate
  7. washwashed with aqueous sodium bicarbonate solution, water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-e9f766759fe546d2808d79227e7ab0ae
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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