Bromine → HCID 19896191, compound

HRID 1196764Notes

Reaction equation

HRID 1196764 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[NH:12][C:11]2=[O:24])=[CH:6][CH:5]=1.[Br:27]Br>C(O)(=O)C>[F:26][C:2]([F:1])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:15](=[O:16])[C:14]([Br:27])=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[NH:12][C:11]2=[O:24])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 19896208HCID 19896208, compound

Product 1

HCID 19896191HCID 19896191, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.8 g of 3-(4-trifluoromethoxyphenyl)-6-(2-chlorophenyl)-2,4(1H,3H)-pyrimidinedione was added to 75 ml of acetic acid, followed by dropwise addition of 1.7 g of bromine to the solution with stirring at room temperature. The reaction mixture was further stirred for 2 hours and then the solvent was distilled away under reduced pressure. The residue was dissolved in 200 ml of ethyl acetate, washed with an aqueous solution of sodium hydrogencarbonate and water, and dried over anhydrous sodium sulfate. Then the solvent was distilled away to obtain 4.5 g of a crude product. This crude crystal product was washed with heated diisopropyl ether and dried to obtain 4.1 g of the objective compound.

Workup

  1. stirringThe reaction mixture was further stirred for 2 hours
  2. distillationthe solvent was distilled away under reduced pressure
  3. dissolutionThe residue was dissolved in 200 ml of ethyl acetate
  4. washwashed with an aqueous solution of sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen the solvent was distilled away
  7. customto obtain 4.5 g of a crude product
  8. washThis crude crystal product was washed with heated diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-5f9256227f1645c9a3ced1569f71d1e5
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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