Isopropylsulphamoyl chloride → Methyl 2-((((1-methylethyl)amino)sulfonyl)amino)-3-pyridine carboxylate

HRID 1439275Notes

Reaction equation

HRID 1439275 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.[CH:12]([NH:15][S:16](Cl)(=[O:18])=[O:17])([CH3:14])[CH3:13]>C1C=CC=CC=1>[CH3:13][CH:12]([NH:15][S:16]([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:18])=[O:17])[CH3:14]

Participants

4

Reactant 2

HCID 117737Isopropylsulphamoyl chlorideHCID 351633Methyl 2-aminopyridine-3-carboxylate

Product 1

HCID 13609242Methyl 2-((((1-methylethyl)amino)sulfonyl)amino)-3-pyridine carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 2-amino-3-pyridine carboxylate (10.0 grams; 0.066 mole) and isopropyl sulfamoyl chloride (11.4 grams; 0.066 mole) were mixed with 300 ml of benzene and the resulting reaction mixture heated at reflux temperatures for a period of 48 hours. Following the reaction period, the reaction mixture was cooled and the solvent removed in vacuo. The oily residue thus obtained was extracted with 200 ml of cyclohexane and the extracts combined and cooled. The resulting precipitate was recovered by filtration and recrystallized from carbon tetrachloride. As a result of these operations, the desired title compound having a melting point of 121°-123° C. was obtained.

Workup

  1. customthe resulting reaction mixture
  2. temperatureheated
  3. temperatureat reflux temperatures for a period of 48 hours
  4. customthe reaction period
  5. temperaturethe reaction mixture was cooled
  6. customthe solvent removed in vacuo
  7. customThe oily residue thus obtained
  8. extractionwas extracted with 200 ml of cyclohexane
  9. temperaturecooled
  10. filtrationThe resulting precipitate was recovered by filtration
  11. customrecrystallized from carbon tetrachloride
  12. customAs a result of these operations

Sources & evidence

ORD record
ord-87b9c6cbca7047359853b8c2a76ea5b0
Source dataset
uspto-grants-1977_11
Patent number
US04058533

Reaction notes

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