Methyl p-toluenesulfonate → HCID 44589226, compound

HRID 2210468Notes

Reaction equation

HRID 2210468 reaction equation
[CH2:1]([N:3]1[C:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[N:12][C:7]=2[S:6](=[O:15])(=[O:14])[NH:5][CH2:4]1)[CH3:2].[OH-].[Na+].[C:18]1(C)C=CC(S(OC)(=O)=O)=CC=1>C(#N)C>[CH3:18][N:5]1[CH2:4][N:3]([CH2:1][CH3:2])[C:8]2[CH:9]=[C:10]([CH3:13])[CH:11]=[N:12][C:7]=2[S:6]1(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 14798Sodium HydroxideHCID 19378719HCID 19378719, compound

Product 1

HCID 44589226HCID 44589226, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 0.2 g of 4-ethyl-6-methyl-2,3- dihydro-4H-pyrido[3,2-e][1,2,4]thiadiazine 1,1-dioxide (Example 79) in 10 cm3 of acetonitrile is treated with 2 equivalents of NaOH and then brought to reflux for 15 minutes with stirring. The mixture is treated with 0.18 g of methyl p-toluenesulfonate and stirred for 2 hours at ambient temperature. The solvent is then removed under reduced pressure and the residue is taken up in 5 cm3 of water. The precipitate is collected on a filter, washed with water and dried. It is purified by chromatography on a silica column (1/1 chloroform/diethyl ether).

Workup

  1. temperatureto reflux for 15 minutes
  2. stirringstirred for 2 hours at ambient temperature
  3. customThe solvent is then removed under reduced pressure
  4. customThe precipitate is collected on a filter
  5. washwashed with water
  6. customdried
  7. customIt is purified by chromatography on a silica column (1/1 chloroform/diethyl ether)

Sources & evidence

ORD record
ord-2f0d701e32714688805d47fd840718a6
Source dataset
uspto-grants-1995_10
Patent number
US05459138

Reaction notes

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