Water → 2-Benzyl-5-methoxy-2H-1,2,4,6-thiatriazin-3-one-1,1-dioxide

HRID 246832Notes

Reaction equation

HRID 246832 reaction equation
[C:1]([NH:5][C:6](=[N:9][S:10](=[O:20])(=[O:19])[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:7][CH3:8])(OC)=[O:2].[H-].[Na+].O>C1COCC1>[CH2:12]([N:11]1[C:1](=[O:2])[NH:5][C:6]([O:7][CH3:8])=[N:9][S:10]1(=[O:20])=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 70392213N-carbomethoxy-N'-benzylsulfamoyl-O-methylisourea

Product 1

HCID 136459252-Benzyl-5-methoxy-2H-1,2,4,6-thiatriazin-3-one-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-carbomethoxy-N'-benzylsulfamoyl-O-methylisourea (215 g) in anhydrous THF (200 ml) is added dropwise to a stirred suspension of sodium hydride (43 g of 60% dispersion) in anhydrous THF (900 ml) and refluxed for 2 hours under nitrogen. Water (800 ml) is added to the cooled reaction mixture and the aqueous mixture washed with ether. The pH of the aqueous layer is adjusted to about 3.2 and the resulting suspension extracted with methylene chloride. The methylene chloride extract is dried, filtered, and evaporated in vacuo. The residue is taken up in hot isopropyl alcohol, treated with charcoal, filtered hot, concentrated, cooled, the resulting precipitate filtered and dried in vacuo yielding the desired product, M.P.=141°-144° C.

Workup

  1. temperaturerefluxed for 2 hours under nitrogen
  2. washthe aqueous mixture washed with ether
  3. extractionthe resulting suspension extracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. customis dried
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. additiontreated with charcoal
  9. filtrationfiltered hot
  10. concentrationconcentrated
  11. temperaturecooled
  12. filtrationthe resulting precipitate filtered
  13. customdried in vacuo

Sources & evidence

ORD record
ord-09475bbdd5da410191ed914a91abd805
Source dataset
uspto-grants-1987_11
Patent number
US04704388

Reaction notes

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