Chlorosuccinimide → 5-Chloro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1905871Notes

Reaction equation

HRID 1905871 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH3:17])[C:15](=[O:18])[N:14]([CH3:19])[C:13](=[O:20])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:21]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:21][C:12]1[C:13](=[O:20])[N:14]([CH3:19])[C:15](=[O:18])[N:16]([CH3:17])[C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 140964656-(3,4-dimethoxyphenyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 136081945-Chloro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneYield 79.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (2.0 g) in acetic acid (100 ml) was added N-chlorosuccinimide (0.97 g), and the mixture was stirred at 100° C. for 5 hours. After cooling, the reaction mixture was evaporated, and dissolved in chloroform, The solution was washed with aqueous sodium bicarbonate, and dried over magnesium sulfate. After removal of the solvent, resulting mass was crystallized from ethanol, to give 5-chloro-6-(3,4-dimethoxyphenyl)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione (1.79 g).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. dissolutiondissolved in chloroform
  4. washThe solution was washed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent
  7. customresulting mass
  8. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-45a878eb67ed4dae89c067d67f5137bd
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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