2,5-Dichloroaniline → HCID 18549210, compound

HRID 1266192Notes

Reaction equation

HRID 1266192 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].[H-].[Na+].[CH2:12]([N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=[C:15]1SC)[CH3:13].C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH:4][C:15]1[N:14]([CH2:12][CH3:13])[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[N:16]=1

Participants

6

Reactant 4

HCID 72622,5-DichloroanilineHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 18549213HCID 18549213, compound

Product 1

HCID 18549210HCID 18549210, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,5-Dichloroaniline (0.49 g, 3.0 mmol) was dissolved in DMF (20 ml), and sodium hydride (60% oil, 0.20 g, 5.01 mmol) was added, followed by stirring at room temperature for 20 minutes. Then, 3-ethyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (1,14 g, 4.80 mmol) synthesized in the above was added, followed by stirring at 80° C. for 4 hours. After completion of the reaction, ice-water (30 ml) and ethyl acetate (30 ml) were added to the reaction solution to separate the organic layer, and then the aqueous layer was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with saturated sodium bicarbonate aqueous solution (50 ml), water (50 ml×2) and saturated brine (80 ml) and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. The thus obtained crude product was purified by a silica gel column chromatography (hexane: ethyl acetate=10:1) and then recrystallized from toluene, thereby obtaining yellow crystals of 2-(2,5-dichlorophenyl)amino-3-ethyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 6].

Workup

  1. additionabove was added
  2. stirringby stirring at 80° C. for 4 hours
  3. additionwere added to the reaction solution
  4. customto separate the organic layer
  5. extractionthe aqueous layer was extracted with ethyl acetate (20 ml×3)
  6. washwashed with saturated sodium bicarbonate aqueous solution (50 ml), water (50 ml×2) and saturated brine (80 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe drying agent was removed by filtration
  9. concentrationthe resulting filtrate was concentrated under a reduced pressure
  10. customThe thus obtained crude product
  11. customwas purified by a silica gel column chromatography (hexane: ethyl acetate=10:1)
  12. customrecrystallized from toluene

Sources & evidence

ORD record
ord-201b4dbf64fe4651bd2765c69118d9a5
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

Loading…