2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → 3-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 380784Notes

Reaction equation

HRID 380784 reaction equation
[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([NH2:6])=[C:4]([F:12])[CH:3]=1.CN(C)[C:15]1[O:16][C:17](=[O:25])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=1>C(O)(=O)C>[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([N:6]2[C:17](=[O:25])[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[NH:20][C:15]2=[O:16])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 137530614-Chloro-2-fluoro-5-nitroaniline

Product 1

HCID 183659053-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-chloro-2-fluoro-5-nitroaniline (5.0 g, 26.3 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (5.73 g, 27.6 mmnol) in acetic acid is refluxed for 4 hours and poured onto ice. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and air-dried to give the title product as a beige solid (7.5 g, 81% yield, mp 230-232° C.) which is identified by 1H, 13C and 19F NMR spectral analyses.

Workup

  1. additionpoured onto ice
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. washThe solid is washed with water
  5. customair-dried

Sources & evidence

ORD record
ord-13aecc7216074e85a2ede8a82650e594
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

Loading…