Methyl iodide → Methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 2255879Notes

Reaction equation

HRID 2255879 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[F:9][C:10]1[CH:11]=[CH:12][C:13]([N+:30]([O-:32])=[O:31])=[C:14]([N:16]2[C:21](=[O:22])[NH:20][C:19](=[O:23])[N:18]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:17]2=[O:29])[CH:15]=1>CN(C)C=O.C(OCC)(=O)C.CCOCC>[F:9][C:10]1[CH:11]=[CH:12][C:13]([N+:30]([O-:32])=[O:31])=[C:14]([N:16]2[C:21](=[O:22])[N:20]([CH3:3])[C:19](=[O:23])[N:18]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:17]2=[O:29])[CH:15]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11067766methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 57274056Methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

Methyl iodide (5.0 mL, 80.31 mmol) and potassium carbonate (11.12 g, 80.45 mmol) are added to a solution of methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (25.65 g, 75.40 mmol) in N,N-dimethylformamide. The reaction mixture is stirred at room temperature overnight, concentrated in vacuo and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 0.08M sodium metabisulfite solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow oil. The oil is dissolved in a refluxing ethyl acetate/ether (1:1) solution and the resultant solution is chilled and treated dropwise with hexanes to obtain a solid. The solid is collected, washed with an ether/ethyl acetate/hexanes (1:1:8) solution and dried overnight in vacuo at 50° C. to give the title product as a solid, mp 121.8°-122.3° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionpoured into water
  3. extractionThe aqueous mixture is extracted with ethyl acetate
  4. washwashed sequentially with water, 0.08M sodium metabisulfite solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a yellow oil
  8. customto obtain a solid
  9. customThe solid is collected
  10. washwashed with an ether/ethyl acetate/hexanes (1:1:8) solution
  11. customdried overnight in vacuo at 50° C.

Sources & evidence

ORD record
ord-729fe5abe5764f0aa6f39308f15dfb7b
Source dataset
uspto-grants-1997_08
Patent number
US05654256

Reaction notes

Loading…