Methyl p-toluenesulfonate → HCID 10560540, compound

HRID 2210462Notes

Reaction equation

HRID 2210462 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[NH:4][CH2:3]1.[C:14](=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(OC)(=O)=O)=CC=1>C(#N)C>[CH3:14][N:4]1[CH2:3][N:2]([CH3:1])[C:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]=2[S:5]1(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 10845683HCID 10845683, compound

Product 1

HCID 10560540HCID 10560540, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.25 g of 4-methyl-2,3-dihydro-4H- pyrido[4,3e][1,2,4]thiadiazine 1,1-dioxide (Example 5) in 8 cm3 of acetonitrile is treated with 0.5 g of potassium carbonate (±3 eq.) and then with 0.26 g of methyl p-toluenesulfonate (1.1 eq.). The suspension obtained is brought to reflux for 2 hours. The solvent is then removed by evaporation under reduced pressure and the residue is distributed between 10 cm3 of water and 100 ml of chloroform. The aqueous phase is then extracted twice with 50 cm3 of chloroform. The combined organic fractions are dried over MgSO4, filtered and then concentrated to dryness. The residue is dissolved in the minimum amount of chloroform. The addition of an excess of petroleum ether (40°-60° C.) causes precipitation of the crystals of the title product. They are collected on the filter, washed with petroleum ether (40°-60° C.) and dried. Yd. : 60-65%

Workup

  1. customThe suspension obtained
  2. temperatureto reflux for 2 hours
  3. customThe solvent is then removed by evaporation under reduced pressure
  4. extractionThe aqueous phase is then extracted twice with 50 cm3 of chloroform
  5. dry with materialThe combined organic fractions are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. dissolutionThe residue is dissolved in the minimum amount of chloroform
  9. additionThe addition of an excess of petroleum ether (40°-60° C.)
  10. customprecipitation of the crystals of the title product
  11. customThey are collected on the filter
  12. washwashed with petroleum ether (40°-60° C.)
  13. customdried

Sources & evidence

ORD record
ord-cc556e6a094a450f879fd494c4774579
Source dataset
uspto-grants-1995_10
Patent number
US05459138

Reaction notes

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