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

HRID 66699Notes

Reaction equation

HRID 66699 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:7]([N:9]1[S:14](=[O:16])(=[O:15])[NH:13][C:12]([O:17][CH3:18])=[N:11][C:10]1=O)[CH3:8].P(Cl)(Cl)([Cl:22])=O>>[Cl:22][C:10]1[N:9]([CH2:7][CH3:8])[S:14](=[O:16])(=[O:15])[N:13]=[C:12]([O:17][CH3:18])[N:11]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178462975HCID 178462975, compound

Product 1

HCID 1571962H-1,2,4,6-Thiatriazine, 3-chloro-2-ethyl-5-methoxy-, 1,1-dioxideYield 91%

Procedure

154 parts of phosphorus pentachloride were added, in the course of 2 minutes, to a stirred mixture of 128 parts of 6-ethyl-3-methoxy-6H-1,2,4,6-thiatriazin-5-one-1,1-dioxide in 840 parts of phosphorus oxychloride, at 25° C. The reaction mixture was stirred under reflux for 51/2 hours and then concentrated under reduced pressure. The oil which remained was taken up in 300 parts of 1,2-dichloroethane and chromatographed over neutral alumina (activity I). The solution was then evaporated down, giving 127.5 parts (91% of theory) of 5-chloro-6-ethyl-3-methoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide, of melting point 63°-70° C.

Workup

  1. temperatureunder reflux for 51/2 hours
  2. concentrationconcentrated under reduced pressure
  3. customchromatographed over neutral alumina (activity I)
  4. customThe solution was then evaporated down

Sources & evidence

ORD record
ord-e2da58220998410e8bf83cbca7959dd5
Source dataset
uspto-grants-1982_08
Patent number
US04343648

Reaction notes

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