Hydrochloric Acid → 3-Methyl-2lambda~6~-pyrido[2,3-c][1,2,6]thiadiazine-2,2,4(1H,3H)-trione

HRID 66036Notes

Reaction equation

HRID 66036 reaction equation
[CH3:1][NH:2][S:3]([NH:6][C:7]1[C:12]([C:13]([O:15]C)=O)=[CH:11][CH:10]=[CH:9][N:8]=1)(=[O:5])=[O:4].C[O-].[Na+].Cl>CO.O>[CH3:1][N:2]1[S:3](=[O:5])(=[O:4])[NH:6][C:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]1=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22756775Methyl 2-(((methylamino)sulfonyl)amino)-3-pyridine carboxylate

Product 1

HCID 542381953-Methyl-2lambda~6~-pyrido[2,3-c][1,2,6]thiadiazine-2,2,4(1H,3H)-trione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 2-(((methylamino)sulfonyl)amino)-3-pyridine carboxylate (11.0 grams; 0.045 mole) was dissolved in 150 ml of methanol and sodium methoxide (7.3 grams; 0.135 mole) added thereto. The resulting reaction mixture was heated at reflux temperatures for a period of about 4 hours. After cooling the reaction mixture, the solvent was removed in vacuo and the residue thus obtained suspended in 30 ml of water and the resulting suspension acidified to a pH of about 1.0 with concentrated hydrochloric acid. The reaction mixture was filtered and the precipitate thus obtained was washed with several portions of water and dried in vacuo. As a result of such operations, the desired title compound was obtained as a white powder having a melting point of 290° C.-292° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux temperatures for a period of about 4 hours
  4. temperatureAfter cooling the reaction mixture
  5. customthe solvent was removed in vacuo
  6. customthe residue thus obtained
  7. filtrationThe reaction mixture was filtered
  8. customthe precipitate thus obtained
  9. washwas washed with several portions of water
  10. customdried in vacuo
  11. customAs a result of such operations

Sources & evidence

ORD record
ord-a24881d89d014af98cdd3342ceb06829
Source dataset
uspto-grants-1978_12
Patent number
US04129734

Reaction notes

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