Bromine → HCID 19896194, compound

HRID 1196776Notes

Reaction equation

HRID 1196776 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[NH:12][C:11]1=[O:21].C([O-])(=O)C.[Na+].[Br:27]Br>C(O)(=O)C>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:15](=[O:16])[C:14]([Br:27])=[C:13]([C:17]([F:20])([F:19])[F:18])[NH:12][C:11]1=[O:21]

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 19896218HCID 19896218, compound

Product 1

HCID 19896194HCID 19896194, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.6 g of 3-(2,4,6-trichlorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione and 4.1 g of sodium acetate were added to 30 ml of acetic acid, followed by dropwise addition of 6.4 g of bromine with stirring at room temperature. The resulting solution was stirred at 110° C. for 5 hours and then the solvent was distilled away under reduced pressure. The residue was extracted with 100 ml of ethyl acetate, and the obtained organic layer was washed with water and dried. Then the solvent was distilled away to obtain a crude product. This crude product was washed with isopropyl ether and dried to obtain 1.8 g of the objective compound.

Workup

  1. stirringThe resulting solution was stirred at 110° C. for 5 hours
  2. distillationthe solvent was distilled away under reduced pressure
  3. extractionThe residue was extracted with 100 ml of ethyl acetate
  4. washthe obtained organic layer was washed with water
  5. customdried
  6. distillationThen the solvent was distilled away
  7. customto obtain a crude product
  8. washThis crude product was washed with isopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-ba1ce4b255784a0087f4ce362eea8c27
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

Loading…