Chlorosuccinimide → HCID 19987104, compound

HRID 973912Notes

Reaction equation

HRID 973912 reaction equation
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][CH:11]([CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15])[C:4](=[O:18])[CH:3]=1.[Cl:19]N1C(=O)CCC1=O>C(#N)C>[Cl:19][C:3]1[C:4](=[O:18])[N:5]([CH2:10][CH:11]([CH2:16][CH3:17])[CH2:12][CH2:13][CH2:14][CH3:15])[C:6](=[O:9])[N:7]([CH3:8])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 19987105HCID 19987105, compound

Product 1

HCID 19987104HCID 19987104, compoundYield 111.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a solution containing 20 g of 6-chloro-3-(2-ethylhexyl)-1-methyluracil thus-obtained in 50 ml of acetonitrile was added 8.6 g of N-chlorosuccinimide, the mixture was heated to 40° C. and stirred for 2 hours. After allowing the mixture to cool, the acetonitrile was distilled off under reduced pressure, to the residue was added water and it was extracted with 100 ml of chloroform. The organic phase was washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The chloroform was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain 22 g of 5,6-dichloro-3-(2-ethylhexyl)-1-methyluracil as an oily product.

Workup

  1. temperatureto cool
  2. distillationthe acetonitrile was distilled off under reduced pressure, to the residue
  3. additionwas added water and it
  4. extractionwas extracted with 100 ml of chloroform
  5. washThe organic phase was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe chloroform was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f593d09ffeea4c11ad906ff919de8352
Source dataset
uspto-grants-1991_11
Patent number
US05066573

Reaction notes

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