Trimethyl phosphite → Phosphonic acid, (5-methoxy-2-methyl-1,1-dioxido-2H-1,2,4,6-thiatriazin-3-yl)-, dimethyl ester

HRID 2418130Notes

Reaction equation

[P:1]([O:6]C)([O:4][CH3:5])[O:2][CH3:3].Cl[C:9]1[N:14]([CH3:15])[S:13](=[O:17])(=[O:16])[N:12]=[C:11]([O:18][CH3:19])[N:10]=1>C1(C)C=CC=CC=1>[CH3:15][N:14]1[S:13](=[O:17])(=[O:16])[N:12]=[C:11]([O:18][CH3:19])[N:10]=[C:9]1[P:1]([O:2][CH3:3])([O:4][CH3:5])=[O:6]

Participants

Conditions

Temperature: 70 °C

Procedure

145 parts of trimethyl phosphite were added, in the course of 40 minutes, to 165 parts of 5-chloro-6-methyl-3-methoxy-6H-1,2,4,6-thiatriazine-1,1-dioxide in 550 parts of toluene at from 38° to 41° C., while stirring. The reaction mixture was heated to 70° C. in the course of 30 minutes, and stirring was continued at this temperature for 13/4 hours. Thereafter, the solution was decanted off from the small amount of tacky residue, and was freed from volatile constituents at 80° C./0.2 mbar. The residue was dissolved in 300 parts of ethyl acetate, and the solution was chromatographed over neutral aluminum oxide. After evaporating down under reduced pressure, 192 parts (96% of theory) of 6-methyl-3-methoxy-5-dimethylphosphono-6H-1,2,4,6-thiatriazine-1,1-dioxide of nD25 =1.4998 were obtained.

Workup

stirringstirring
custom4 hours
customThereafter, the solution was decanted off from the small amount of tacky residue
customwas freed from volatile constituents at 80° C.
dissolutionThe residue was dissolved in 300 parts of ethyl acetate
customthe solution was chromatographed over neutral aluminum oxide
customAfter evaporating down under reduced pressure, 192 parts (96% of theory) of 6-methyl-3-methoxy-5-dimethylphosphono-6H-1,2,4,6-thiatriazine-1,1-dioxide of nD25 =1.4998
customwere obtained

Sources & evidence

ORD record: ord-604ddd00fd4f4c379fb069147af97132
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472191

Reaction notes

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