Hydrochloric Acid → 3-[4-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1722978

Reaction equation

HRID 1722978 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]([F:34])=[C:31]([F:33])[F:32].Cl>O>[Cl:1][C:2]1[C:7]([O:8][C:31]([F:33])([F:32])[CH:30]([Cl:29])[F:34])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6594Chlorotrifluoroethylene2×HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 200261363-[4-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.0 g of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6 -trifluoromethyl-2,4(1H,3H)pyrimidinedione is treated with 0.25 g of potassium carbonate and the suspension is saturated with chlorotrifluoroethylene while stirring during 10 minutes. The reaction mixture is subsequently heated to 50° C. for 10 minutes, during which a slow stream of chlorotrifluoroethylene is conducted in. Thereafter, the reaction mixture is poured into a solution of 3 ml of 2N hydrochloric acid in 250 ml of water, and the whole is extracted with 100 ml of ethyl acetate. The organic phase is washed neutral with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The resinous residue is purified by chromatography on a silica gel column using diethyl ether/n-hexane (1:3) as the eluent. There is obtained 3-[4-chloro-5-(2-chloro-1,1,2-trifluoroethoxy)-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 1H-NMR (CDCl3, 400 MHz : 7.40 ppm (d,1H), 7.32 ppm (m,1H), 6.37 ppm (s,1H), 6.33 ppm (m,1H), 3.57 ppm (d,3H).

Workup

  1. extractionthe whole is extracted with 100 ml of ethyl acetate
  2. washThe organic phase is washed neutral with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to dryness under reduced pressure
  5. customThe resinous residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-c2ab1cf2a89e4a5bac93d78dc6873dac
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Linked notes

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