m-Chloroperbenzoic acid → HCID 53868015, compound

HRID 1722973Notes

Reaction equation

HRID 1722973 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:18]([O:19][CH2:20][S:21][CH3:22])=[CH:17][C:16]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])=[C:15]([F:36])[CH:14]=1>[Cl-].C(Cl)Cl>[Cl:12][C:13]1[C:18]([O:19][CH2:20][S:21]([CH3:22])=[O:9])=[CH:17][C:16]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:25]([CH3:34])[C:24]2=[O:35])=[C:15]([F:36])[CH:14]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1353992,4(1H,3H)-Pyrimidinedione, 3-(4-chloro-2-fluoro-5-((methylthio)methoxy)phenyl)-1-methyl-6-(trifluoromethyl)-

Product 1

HCID 53868015HCID 53868015, compound

Reagents, catalysts & solvents 2

HCID 312ChlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 3-chloro-perbenzoic acid in 15 ml of metyylene chloride is added dropwise while stirring at 0° C. during 1 hour to a solution of 2.3 g of 1-[4-chloro-2-fluoro-5 -(methylthio)methoxy-phenyl]-3-methyl-4-trifluoromethyl-2,6-(1H,3H)-pyrimidinedione in 30 ml of methylene chloride. The reaction mixture is subsequently stirred at room temperature for 15 hours, washed with dilute aqueous sodium bicarbonate solution and then with water and dried over anhydrous sodium sulphate. The organic phase is evaporated to dryness under reduced pressure and the residue is purified by chromatography on a silica gel column using diethyl ether/ethyl acetate and thereafter ethyl acetate alone as the eluent. There is obtained 1-[4-chloro-2-fluoro-5-(methylsulphinyl) methoxy-phenyl]-3-methyl-4-trifluoromethyl-2,6(1H,3H)pyrimidinedione, 1H-NMR (CDCl3, 400 MHz): 7.33 ppm (d.1H). 7.27 ppm (2d,1H), 6.34 ppm (2s,1H). 4.91-5.05 ppm (m,2H), 3.54 ppm (d,3H), 2.72 ppm (s,3H).

Workup

  1. washwashed with dilute aqueous sodium bicarbonate solution
  2. dry with materialwith water and dried over anhydrous sodium sulphate
  3. customThe organic phase is evaporated to dryness under reduced pressure
  4. customthe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-9cabb42f73ac4e2482d6f49a30c88c10
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

Loading…