N,N-Dimethylcyclohexylamine → 2,5-Dimethyl-3-[(pyridin-3-yl)oxy]-1lambda~6~,2,4,6-thiatriazine-1,1(2H)-dione
Reaction equation
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([OH:7])[CH:2]=1.CN(C1CCCCC1)C.[CH3:17][N:18]1[C:23](Cl)=[N:22][C:21]([CH3:25])=[N:20][S:19]1(=[O:27])=[O:26]>C(Cl)Cl>[CH3:17][N:18]1[C:23]([O:7][C:3]2[CH:4]=[N:5][CH:6]=[CH:1][CH:2]=2)=[N:22][C:21]([CH3:25])=[N:20][S:19]1(=[O:27])=[O:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
17.1 parts of β-hydroxypyridine in 120 parts of methylene chloride and 19.1 parts of N,N-dimethylcyclohexylamine are introduced simultaneously, via 2 feeds, in the course of 15 minutes and at 15°-20° C., into a stirred solution of 29.3 parts of 2,5-dimethyl-3-chloro-2H-1,2,4,6-thiatriazine 1,1-dioxide in 150 parts of methylene chloride. The mixture is stirred for one hour at 25° C., after which the precipitate is filtered off under suction and the filtrate is washed with water and with dilute sodium carbonate solution, dried over magnesium sulfate, chromatographed over neutral aluminum oxide and then evaporated down under reduced pressure to give 26 parts (68.6% of theory) of 2,5-dimethyl-3-(pyrid-3-yloxy)-2H-1,2,4,6-thiatriazine 1,1-dioxide of melting point 137°-138° C. (compound No. 1).
Workup
- filtrationafter which the precipitate is filtered off under suction
- washthe filtrate is washed with water and with dilute sodium carbonate solution
- dry with materialdried over magnesium sulfate
- customchromatographed over neutral aluminum oxide
- customevaporated down under reduced pressure
Sources & evidence
- ORD record
- ord-9792fc34d7f3477c95387079944cfcc0
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04585472
Reaction notes
Loading…