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

HRID 1742919Notes

Reaction equation

HRID 1742919 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])[CH3:17]>>[NH2:3][C:4]1[N:9]=[C:8]([O:18][CH2:16][CH3:17])[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 150103952-Amino-4-ethoxy-6-trifluoromethoxy-1,3,5-triazine

Procedure

2.3 g (0.093 mol) of 97% sodium hydride were added a little at a time to 300 ml of ethanol at 20°-35° C. and dissolved by stirring for 15 minutes. Then, while stirring at 0° C., 18.5 g (0.093 mol) of 2-amino-4-fluoro-6-trifluoromethoxy-1,3,5-triazine were added over the course of 10 minutes, and the mixture was stirred at 0° C. for 1 hour and at 22° C. overnight. The residue from concentration under reduced pressure was taken up in methylene chloride, extracted with water and dried. Concentration yielded 17.9 g (85.9% of theory) of the title compound of melting point 69°-71° C.

Workup

  1. dissolutiondissolved
  2. stirringThen, while stirring at 0° C.
  3. stirringthe mixture was stirred at 0° C. for 1 hour and at 22° C. overnight
  4. concentrationThe residue from concentration under reduced pressure
  5. extractionextracted with water
  6. customdried
  7. concentrationConcentration

Sources & evidence

ORD record
ord-0d090a0f528346478919ea4d13167296
Source dataset
uspto-grants-1994_08
Patent number
US05342939

Reaction notes

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