Chlorosuccinimide → HCID 18549196, compound

HRID 1266204Notes

Reaction equation

HRID 1266204 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[NH:13][C:14]1[N:19]([CH:20]([CH2:22][CH3:23])[CH3:21])[C:18](=[O:24])[CH:17]=[C:16]([C:25]([F:28])([F:27])[F:26])[N:15]=1.[Cl:31]N1C(=O)CCC1=O>ClCCl>[F:30][C:2]([F:29])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:11])([F:10])[F:12])=[CH:5][C:4]=1[NH:13][C:14]1[N:19]([CH:20]([CH2:22][CH3:23])[CH3:21])[C:18](=[O:24])[C:17]([Cl:31])=[C:16]([C:25]([F:26])([F:27])[F:28])[N:15]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18549188HCID 18549188, compound

Product 1

HCID 18549196HCID 18549196, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A dichloromethane (10 ml) solution of 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-sec-butyl-6-trifluoromethyl-4(3H)-pyrimidinone (430 mg, 0.96 mmol) and N-chlorosuccinimide (141 mg, 1.06 mmol) was heated under reflux for 4 hours. After completion of the reaction, the solvent was evaporated under a reduced pressure, the resulting residue was suspended in ether (20 ml) and then the solid deposited was filtered. The resulting filtrate was washed with saturated sodium bicarbonate aqueous solution and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated under a reduced pressure. By purifying the thus obtained residue by a silica gel column chromatography (toluene), 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-sec-butyl-5-chloro-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 59] was obtained as colorless crystals.

Workup

  1. temperatureunder reflux for 4 hours
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated under a reduced pressure
  4. filtrationthe solid deposited was filtered
  5. washThe resulting filtrate was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under a reduced pressure
  8. customBy purifying the thus obtained residue by a silica gel column chromatography (toluene)

Sources & evidence

ORD record
ord-a76466b900774cdea8edd5b62fb1a256
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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