Trifluoroacetic acid → Dihydro-1-[3-(monofluoromethyl)phenyl]-1,2,4-triazine-3,5-(2H,4H)-dione

HRID 1493625Notes

Reaction equation

HRID 1493625 reaction equation
NN.[F:3][CH2:4][C:5]1[CH:6]=[C:7]([N:11]([CH2:13][C:14]([O:16]C)=O)[NH2:12])[CH:8]=[CH:9][CH:10]=1.[O-:18][C:19]#[N:20].[Na+].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[F:3][CH2:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:13][C:14](=[O:16])[NH:20][C:19](=[O:18])[NH:12]2)[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 517096Sodium CyanateHCID 54347809HCID 54347809, compound

Product 1

HCID 19829890Dihydro-1-[3-(monofluoromethyl)phenyl]-1,2,4-triazine-3,5-(2H,4H)-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The hydrazine (Intermediate 55, 1.5 g, 7.1 mmol) was dissolved in dry toluene (30 ml) under nitrogen at room temperature. Sodium cyanate (1.6 g, 24.6 mmol) was added followed by trifluoroacetic acid (1.7 ml, 22,1 mmol). The reaction was stirred for 2.25 h after which the reaction was poured into saturated sodium bicarbonate solution (100 ml) and extracted with ethyl acetate (4×(100 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give a white solid. The crude material was triturated with ether (2×100 ml) to give the title compound (Intermediate 56, 1.41 g, 78%) as a colourless powder, m.p. 169°-70°.

Workup

  1. extractionextracted with ethyl acetate (4×(100 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customto give a white solid
  5. customThe crude material was triturated with ether (2×100 ml)

Sources & evidence

ORD record
ord-dbadf34546d546a6a37a2b47c582bac9
Source dataset
uspto-grants-1991_06
Patent number
US05023255

Reaction notes

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