Methanol → HCID 2799819, compound

HRID 430442Notes

Reaction equation

HRID 430442 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:7]=1.[CH3:20]O>>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:20])=[O:11])=[C:8]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 2423231HCID 2423231, compound

Product 1

HCID 2799819HCID 2799819, compound

Procedure

Thionyl chloride (21 ml) was added to methanol at 10° C. and the solution stirred for 0.5 hours before being added to 4-chloro-2-(methylsulphonylamino)benzoic acid (11.1 g). The mixture was heated under reflux conditions for 2 days after which time a further addition of thionyl chloride (6 ml) was made and reflux resumed for a further 2 days. The solvent was evaporated to dryness, water added and the mixture extracted with ethyl acetate. The extract was washed with sodium hydroxide solution (2N) then with water, dried (magnesium sulphate) and evaporated to dryness to give methyl 4-chloro-2-(methylsulphonylamino)benzoate (3.85 g) as a cream solid, NMR (CDCl3) 3.25(s,3H), 3.9(s,3H), 7.3(dd,1H), 7.6(m,1H), 7.95(d,1H), 10.2(brs,1H).

Workup

  1. temperatureThe mixture was heated under reflux conditions for 2 days after which time
  2. temperaturereflux
  3. waitresumed for a further 2 days
  4. customThe solvent was evaporated to dryness, water
  5. additionadded
  6. extractionthe mixture extracted with ethyl acetate
  7. washThe extract was washed with sodium hydroxide solution (2N)
  8. dry with materialwith water, dried (magnesium sulphate)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-8155518015894bb998384af1e1cb37b5
Source dataset
uspto-grants-2001_11
Patent number
US06323155B1

Reaction notes

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