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

HRID 1447157Notes

Reaction equation

HRID 1447157 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 and 840 parts of phosphorus oxychloride at 25° C. The reaction mixture was then stirred for 51/2 hours under reflux, after which it was evaporated down under reduced pressure. The oil which remained was taken up in 300 parts of 1,2-dichloroethane and the solution was chromatographed over neutral alumina (Activity I). After evaporating down, 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., were obtained (Compound No. 2).

Workup

  1. temperatureunder reflux
  2. customafter which it was evaporated down under reduced pressure
  3. customthe solution was chromatographed over neutral alumina (Activity I)
  4. customAfter evaporating down

Sources & evidence

ORD record
ord-540abc6c3b5e4fd1bda0b312b9d8772b
Source dataset
uspto-grants-1982_02
Patent number
US04316015

Reaction notes

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