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

HRID 66040

Reaction equation

HRID 66040 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° C.-139° C. was obtained.

Workup

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

Sources & evidence

ORD record
ord-a825db44aa0a4164abb7535f1b9e3a48
Source dataset
uspto-grants-1978_12
Patent number
US04129734

Linked notes

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