Ethanol → 6-Isopropyl-3-methoxy-5-ethoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide

HRID 66702Notes

Reaction equation

HRID 66702 reaction equation
Cl[C:2]1[N:7]([CH:8]([CH3:10])[CH3:9])[S:6](=[O:12])(=[O:11])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.C(N(CC)CC)C.[CH2:22]([OH:24])[CH3:23]>>[CH:8]([N:7]1[S:6](=[O:12])(=[O:11])[N:5]=[C:4]([O:13][CH3:14])[N:3]=[C:2]1[O:24][CH2:22][CH3:23])([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 1571982H-1,2,4,6-Thiatriazine, 3-chloro-5-methoxy-2-(1-methylethyl)-,1,1-dioxide

Product 1

HCID 127859266-Isopropyl-3-methoxy-5-ethoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide

Conditions

Temperature
25 °C

Procedure

28.7 parts by weight of 5-chloro-6-isopropyl-3- methoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide were added, a little at a time, in the course of 10 minutes, to a stirred mixture of 12.2 parts of triethylamine and 90 parts of absolute ethanol at 20°-25° C. After 3 hours' stirring at 25° C., the reaction mixture was evaporated down under reduced pressure, the residue was taken up in methylene chloride and the solution was washed with 10% strength sodium carbonate solution. After drying over magnesium sulfate, chromatography over alumina and evaporating down under reduced presure, 24 parts of 6-isopropyl-33-methoxy-5-ethoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide, of melting point 81°-85° C. were obtained.

Workup

  1. customthe reaction mixture was evaporated down under reduced pressure
  2. washthe solution was washed with 10% strength sodium carbonate solution
  3. dry with materialAfter drying over magnesium sulfate, chromatography over alumina
  4. customevaporating down
  5. customof melting point 81°-85° C. were obtained

Sources & evidence

ORD record
ord-c3ccf01131144a0aa8a185f56a6988de
Source dataset
uspto-grants-1982_08
Patent number
US04343648

Reaction notes

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