Ammonia → 2-Amino-4-fluoro-6-chlorodifluoromethoxy-1,3,5-triazine
Reaction equation
[NH3:1].F[CH:3]1[N:8]=[C:7]([F:9])[N:6]=[C:5]([Cl:10])[N:4]1[O:11][CH:12]([F:14])[F:13]>O1CCCC1>[NH2:1][CH:3]1[N:8]=[C:7]([F:9])[N:6]=[C:5]([Cl:10])[N:4]1[O:11][CH:12]([F:14])[F:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
7.8 g (0.46 mol) of ammonia were passed into a mixture of 50.0 g (0.23 mol) of 2,4-difluoro-6-chlorodifluoromethoxy-1,3,5-triazine in 150 ml of tetrahydrofuran in the course of 45 minutes at -70° C. while stirring. Stirring was carried out for 2 hours at -70° C. and overnight while the mixture warmed up to 22° C. The reaction mixture was evaporated down under reduced pressure and the residue was washed with water and dried. The reaction product was then suspended in methylene chloride, the suspension was applied to a silica gel column and elution was carried out with the same solvent. 21.5 g (43.6% of theory) of 2-amino-4-fluoro-6-chlorodifluoromethoxy-1,3,5-triazine of melting point 131°-133° C. were obtained in fractions 1 to 8. By further eluting with ethyl acetate, the more sparingly soluble 2,4-diamino-6-chlorodifluoromethoxy-1,3,5-triazine (11.2 g, 23% of theory) of melting point 114° C. was then isolated in fractions 9 to 14.
Workup
- stirringStirring
- customThe reaction mixture was evaporated down under reduced pressure
- washthe residue was washed with water
- customdried
- washthe suspension was applied to a silica gel column and elution
Sources & evidence
- ORD record
- ord-1f04f4b3248d4486b15708108c6ede8f
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05434124
Reaction notes
Loading…