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

HRID 246838Notes

Reaction equation

HRID 246838 reaction equation
C([N:5]([S:10](=[O:19])(=[O:18])[NH:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6](=[NH:9])[O:7][CH3:8])(OC)=O.[H-].[Na+].O.C1C[O:26][CH2:25]C1>>[CH:12]1([N:11]2[C:25](=[O:26])[NH:9][C:6]([O:7][CH3:8])=[N:5][S:10]2(=[O:18])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 21269103N-Carbomethoxy-N-cyclohexylsulfamyl-O-methylisourea

Product 1

HCID 130177642-Cyclohexyl-5-methoxy-2H-1,2,4,6-thiatriazin-3-one-1,1-dioxide

Procedure

A solution of the isourea from Step 1. above (208.9 g) in anhydrous THF (500 ml) is added dropwise to a stirred suspension of 60% sodium hydride dispersion (57.0 g) in anhydrous THF (750 ml) and the reaction mixture is refluxed for 2 hours. Distilled water (450 ml) is added dropwise to the stirred mixture which is washed with diethyl ether. 20% sulfuric acid (400 ml) is added slowly to the stirred reaction mixture, which is extracted with methylene chloride, dried, filtered, and the filtrate evaporated and dried under high vacuum yielding the desired product as a crude solid which is used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture is refluxed for 2 hours
  2. washis washed with diethyl ether
  3. addition20% sulfuric acid (400 ml) is added slowly to the stirred reaction mixture, which
  4. extractionis extracted with methylene chloride
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate evaporated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-952999eb7ff04ae597e82dbb5cfa7816
Source dataset
uspto-grants-1987_11
Patent number
US04704388

Reaction notes

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