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

HRID 2296239Notes

Reaction equation

[CH3:1][N:2]1[C:7](=O)[NH:6][C:5]([CH3:9])=[N:4][S:3]1(=[O:11])=[O:10].P(Cl)(Cl)(Cl)(Cl)[Cl:13].P(Cl)(Cl)(Cl)=O>>[Cl:13][C:7]1[N:2]([CH3:1])[S:3](=[O:11])(=[O:10])[N:4]=[C:5]([CH3:9])[N:6]=1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 24819Phosphorus pentachloride

HCID 1824674H-1,2,4,6-Thiatriazin-3-one, 2,5-dimethyl-1,1-dioxo-

Product 1

HCID 1588652H-1,2,4,6-Thiatriazine, 3-chloro-2,5-dimethyl-, 1,1-dioxideYield 100%

Conditions

Temperature: 110 °C

Procedure

212 parts of 2,5-dimethyl-2H-1,2,4,6-thiatriazin-3-one-1,1-dioxide were introduced into a mixture of 292 parts of phosphorus pentachloride and 1,400 parts of phosphorus oxychloride at room temperature, while stirring. The reaction mixture was heated to 110° C. in the course of 30 minutes, stirred under reflux for 6 hours, and then concentrated under reduced pressure, giving 234 parts (100% of theory) of 3-chloro-2,5-dimethyl-2H-1,2,4,6-thiatriazine-1,1-dioxide of melting point 86°-90° C. (NMR (60 MHz, CDCl3): CH3 -C 2.4δ, CH3 -N 3.68δ).

Workup

stirringstirred
temperatureunder reflux for 6 hours
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7eba6364965544e2b9e6eac22f7c8d1e
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04428766

Reaction notes

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