Water → Isopropyl 3-(2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)acetate

HRID 975764Notes

Reaction equation

HRID 975764 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14](=[O:15])[NH:13][C:12](=[O:16])[N:11]([CH3:17])[C:10]1=[O:18].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28].O>CN(C)C=O.C(Cl)Cl.CCOCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12](=[O:16])[N:13]([CH2:26][C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[C:14]1=[O:15]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 121593Isopropyl bromoacetateHCID 572686601-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione

Product 1

HCID 57141938Isopropyl 3-(2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)acetateYield 92.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (40.9 g, 0.150 mol), potassium carbonate (31.1 g, 0.225 mol) and isopropyl bromoacetate (29.1 mL, 0.225 mol) in N,N-dimethylformamide is stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The organic extract is washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and 0% to 10% ether in methylene chloride solutions gives the title product as a white solid (51.5 g, mp 127°-128° C.).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an oil

Sources & evidence

ORD record
ord-868de349172340708405f1f63a8155c6
Source dataset
uspto-grants-1997_03
Patent number
US05610120

Reaction notes

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