1-Bromo-2-Chloroethane → HCID 18936640, compound

HRID 357099Notes

Reaction equation

HRID 357099 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[C:4](=[O:14])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][Cl:30]>CN(C)C=O>[Cl:1][C:2]1[N:7]([CH2:28][CH2:29][Cl:30])[C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[C:4](=[O:14])[C:3]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 18936730HCID 18936730, compound

Product 1

HCID 18936640HCID 18936640, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 2.43 g (7.7 mmol) of 6-chloro-3-(4-chlorobutyl)-5-phenylpyrimidine-2,4(1H,3H)-dione and 1.70 g (12.3 mmol) of potassium carbonate in 40 ml of N,N-dimethylformamide, 1.25 ml (15 mmol) of 1-bromo-2-chloroethane was added at room temperature, followed by stirring at 60° C. for 2 hours and then at 100° C. for 3 hours. After cooling, the reaction mixture was concentrated to dryness. The residue was dissolved in dichloromethane-water; the organic layer was washed with water and dried. The oily substance obtained by distilling off the solvent was purified by column chromatography (eluent, n-hexane/ethyl acetate=5/1→2/1) to yield 1.56 g (54.5%, white powder) of the desired product.

Workup

  1. additionwas added at room temperature
  2. waitat 100° C. for 3 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated to dryness
  5. dissolutionThe residue was dissolved in dichloromethane-water
  6. washthe organic layer was washed with water
  7. customdried
  8. customThe oily substance obtained
  9. distillationby distilling off the solvent
  10. customwas purified by column chromatography (eluent, n-hexane/ethyl acetate=5/1→2/1)

Sources & evidence

ORD record
ord-a3ba25392be04cbd82a963c7db3e9e6d
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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