Ethanol → 2-Amino-4-methoxy-6-trifluoromethoxy-1,3,5-triazine

HRID 2082262Notes

Reaction equation

HRID 2082262 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[C:8](F)[N:7]=[C:6]([O:11][C:12]([F:15])([F:14])[F:13])[N:5]=1.[CH2:16]([OH:18])C>>[NH2:3][C:4]1[N:9]=[C:8]([O:18][CH3:16])[N:7]=[C:6]([O:11][C:12]([F:15])([F:14])[F:13])[N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 150103882-Amino-4-fluoro-6-trifluoromethoxy-1,3,5-triazin

Product 1

HCID 150103932-Amino-4-methoxy-6-trifluoromethoxy-1,3,5-triazine

Procedure

2.3 g (0.093 mol) of 97% strength sodium hydride were added a little at a time to 300 ml of ethanol at from 20 to 35° C. and stirring was carried out until dissolution was complete, which took 15 minutes. 18.5 g (0.093 mol) of 2-amino-4-fluoro-6-trifluoromethoxy-1,3,5-triazine were then added at 0° C. in the course of 10 minutes, while stirring and stirring was continued for 1 hour at 0° C. and overnight at 22° C. The mixture was evaporated down under reduced pressure, after which the residue was taken up in methylene chloride and the solution was extracted with water and dried. Evaporation gave 17.9 g (85.9% of theory) of the title compound of melting point 69°-91° C.

Workup

  1. dissolutionwas carried out until dissolution
  2. stirringwhile stirring
  3. stirringstirring
  4. waitwas continued for 1 hour at 0° C. and overnight at 22° C
  5. customThe mixture was evaporated down under reduced pressure
  6. extractionthe solution was extracted with water
  7. customdried
  8. customEvaporation

Sources & evidence

ORD record
ord-dab9704d44b143a7b71ffc6d8e6d54fd
Source dataset
uspto-grants-1993_02
Patent number
US05188657

Reaction notes

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