Water → HCID 23042389, compound

HRID 2165800Notes

Reaction equation

HRID 2165800 reaction equation
[Cl:1][C:2]1[CH2:10][C:9]([F:12])(F)[C:8]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[K+].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl.O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([F:12])[C:8]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[N:15]([CH3:24])[C:14]2=[O:25])=[CH:7][C:3]=1[C:4]([O:6][CH2:27][CH:29]1[O:31][CH2:30]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 88606423HCID 88606423, compound

Product 1

HCID 23042389HCID 23042389, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of potassium 2-chloro-4-fluoro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate and 0.6 ml of epichlorohydrin are heated at 70° C. for 3 hours in 25 ml of dimethylformamide. Thereafter, the reaction solution is added to 500 ml of water and adjusted to pH 10 to 11 with a small amount of saturated potassium carbonate solution. It is extracted twice with 300 ml of ethyl acetate. The organic phases are washed twice with 200 ml of water, dried over anhydrous magnesium sulphate and concentrated. The residue is purified by chromatography on silica gel with ethyl acetate/n-hexane. There is obtained 2,3-epoxypropyl 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4 -trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoate as a pale yellow oil, 1H-NMR(D6 -DMSO, 400 MHz): 2.73 (m,1H), 2.85 (m,1H), 32 (m,1H), 3.42 (s,3H), 4.10 (m,1H), 4.69 (m,1H), 6.62 (s,1H), 7.92 (d,1H), 8.11 (d,1H), mass spectrum (m/e): M+ 422(16).

Workup

  1. extractionIt is extracted twice with 300 ml of ethyl acetate
  2. washThe organic phases are washed twice with 200 ml of water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on silica gel with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-ffc24ee8ef104b69a64b54280fe1a7a5
Source dataset
uspto-grants-1990_07
Patent number
US04941909

Reaction notes

Loading…