Phosphorus oxychloride → 2H-1,2,4,6-Thiatriazine, 3-chloro-2-ethyl-5-methyl-, 1,1-dioxide

HRID 2296237Notes

Reaction equation

HRID 2296237 reaction equation
[CH2:1]([N:3]1[C:8](=O)[NH:7][C:6]([CH3:10])=[N:5][S:4]1(=[O:12])=[O:11])[CH3:2].P(Cl)(Cl)([Cl:15])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Cl:15][C:8]1[N:3]([CH2:1][CH3:2])[S:4](=[O:12])(=[O:11])[N:5]=[C:6]([CH3:10])[N:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 1588622H-1,2,4,6-Thiatriazin-3(4H)-one, 2-ethyl-5-methyl-, 1,1-dioxide

Product 1

HCID 1588662H-1,2,4,6-Thiatriazine, 3-chloro-2-ethyl-5-methyl-, 1,1-dioxideYield 93%

Procedure

225 parts of 2-ethyl-5-methyl-2H-1,2,4,6-thiatriazin-3-one-1,1-dioxide were introduced into a mixture of 1,300 parts of phosphorus oxychloride and 292 parts of phosphorus pentachloride in the course of 2 minutes, while stirring. The reaction mixture was stirred under reflux for 7 hours and then concentrated under reduced pressure. The oil which remained was taken up in 350 parts of 1,2-dichloroethane and chromatographed over neutral alumina (activity I). The solution was then evaporated down, giving 230 parts (93% of theory) of 3-chloro-2-ethyl-5-methyl-2H-1,2,4,6-thiatriazine-1,1-dioxide of melting point 57°-59° C. (NMR (60 MHz, CDCl3): CH3 -C 2.3δ, N-CH2 3.68-4.03δ (q), CH3 -C 1.2-1.43δ (t)).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureunder reflux for 7 hours
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed over neutral alumina (activity I)
  5. customThe solution was then evaporated down

Sources & evidence

ORD record
ord-c8f13e1b468445e59f651f299a77d9ec
Source dataset
uspto-grants-1984_01
Patent number
US04428766

Reaction notes

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