Calcium Carbonate → Methyl 2-(((methylamino)sulfonyl)amino)-3-pyridine carboxylate

HRID 1729591Notes

Reaction equation

HRID 1729591 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Ca+2].[CH3:17][NH:18][S:19](Cl)(=[O:21])=[O:20]>C(#N)C>[CH3:17][NH:18][S:19]([NH:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 22756775Methyl 2-(((methylamino)sulfonyl)amino)-3-pyridine carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 2-amino-3-pyridine carboxylate (15.2 grams; 0.1 mole), calcium carbonate (13.0 grams; 0.1 mole) and methylsulfamoyl chloride (13.0 grams; 0.1 mole) were mixed with 200 ml. of acetonitrile and the resulting reaction mixture stirred at ambient temperatures for a period of about 15 hours. Following the reaction period, the reaction mixture was filtered and the solvent removed in vacuo. The semi-solid residue thus obtained was extracted with ethanol. A white crystalline precipitate, obtained by filtering the extract solution, was recrystallized from ethanol and the desired title compound having a melting point of 133°-139° C was obtained.

Workup

  1. customthe reaction period
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent removed in vacuo
  4. customThe semi-solid residue thus obtained
  5. extractionwas extracted with ethanol
  6. customA white crystalline precipitate, obtained
  7. filtrationby filtering the extract solution
  8. customwas recrystallized from ethanol
  9. customwas obtained

Sources & evidence

ORD record
ord-665a0d590f52491b952f1fe1cb148d27
Source dataset
uspto-grants-1976_11
Patent number
US03989507

Reaction notes

Loading…