Phosphorus tribromide → HCID 19896216, compound

HRID 1196781Notes

Reaction equation

HRID 1196781 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17](O)[NH:16][C:15]1=[O:22]>N1C=CC=CC=1>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:7]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([Br:2])[NH:16][C:15]1=[O:22]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178516657HCID 178516657, compound

Product 1

HCID 19896216HCID 19896216, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

10 ml of phosphorus tribromide was added dropwise to 0.60 g of pyridine with stirring at 0° C. and, after stirring this solution at 0° C. for 15 minutes, 1.6 g of the obtained 3-(2,4,6-trichlorophenyl)-6-hydroxy-2,4(1H,3H)-pyrimidinedione was added thereto. The mixed solution was stirred at 80° C. for 3 hours, then added into ice water and extracted with 100 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and then the solvent was distilled away under reduced pressure to form a crude product. This crude product was recrystallized from a mixed solvent of hexane and isopropyl ether to obtain 0.62 g of the objective compound.

Workup

  1. stirringafter stirring this solution at 0° C. for 15 minutes
  2. stirringThe mixed solution was stirred at 80° C. for 3 hours
  3. extractionextracted with 100 ml of ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customto form a crude product
  7. customThis crude product was recrystallized from a mixed solvent of hexane and isopropyl ether

Sources & evidence

ORD record
ord-9a7ebcc13a0343d8b58c9903fbda4d85
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Reaction notes

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