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

HRID 66700Notes

Reaction equation

HRID 66700 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][N:8]1[S:13](=[O:15])(=[O:14])[NH:12][C:11]([O:16][CH2:17][CH3:18])=[N:10][C:9]1=O.P(Cl)(Cl)([Cl:22])=O>ClCCCl>[Cl:22][C:9]1[N:8]([CH3:7])[S:13](=[O:15])(=[O:14])[N:12]=[C:11]([O:16][CH2:17][CH3:18])[N:10]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178467474HCID 178467474, compound

Product 1

HCID 1571972H-1,2,4,6-Thiatriazine, 3-chloro-5-ethoxy-2-methyl-, 1,1-dioxideYield 96.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

50 parts of phosphorus pentachloride were introduced into a stirred mixture of 41.4 parts of 6-methyl-3-ethoxy-6H-1,2,4,6-thiatriazin-5-one-1,1-dioxide in 100 parts of 1,2-dichloroethane and 100 parts of phosphorus oxychloride at room temperature. The reaction mixture was stirred under reflux for 12 hours and then evaporated down under reduced pressure, giving 43.5 parts (96.5% of theory) of 5-chloro-6-methyl-3-ethoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide, of melting point 75°-80° C.

Workup

  1. temperatureunder reflux for 12 hours
  2. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-ca3c6e91e2fb47aa8dee43c56111906e
Source dataset
uspto-grants-1982_08
Patent number
US04343648

Reaction notes

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