Reaction #710462

ord-238c723639fe4eacb68332442c26e1ea

Reaction equation

COS(=O)(=O)OC
dimethyl sulfate
Cc1cc(Cl)cc(C(=O)O)c1N
2-amino-3-methyl-5-chlorobenzoic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[Cl-].[Na+]
sodium chloride
COC(=O)c1cc(Cl)cc(C)c1N
2-amino-3-methyl-5-chlorobenzoic acid methyl ester

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherreacted at 110° C. for 7 hours
  2. 2
    Temperaturecooled to room temperature
  3. 3
    Extractionextracted with acetate ethyl
  4. 4
    Dryingdried over anhydrous sodium sulfate
  5. 5
    Filtrationfiltered
  6. 6
    Otherthe solvent was removed

Procedure

To a 500 mL round-bottom flask, 0.2 mol of 2-amino-3-methyl-5-chlorobenzoic acid having the structural formula of IV-5, 300 mL of DMF and 2.0 grams of potassium carbonate were added, stirred at room temperature for 0.5 hour, dimethyl sulfate was dripped, reacted at 110° C. for 7 hours, and cooled to room temperature, poured into a saturated sodium chloride solution, extracted with acetate ethyl, dried over anhydrous sodium sulfate, filtered and the solvent was removed to obtain a crude product, 35.2 grams of 2-amino-3-methyl-5-chlorobenzoic acid methyl ester having a structural formula of VIII-3 was obtained by column chromatography, and the yield was 88.4%;

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09301529B2uspto-grants-2016_04