Hydrochloric Acid → HCID 18549224, compound

HRID 1266198Notes

Reaction equation

HRID 1266198 reaction equation
[H-].[Na+].[F:3][C:4]([F:17])([F:16])[C:5]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:6]=1[NH2:7].[CH2:18]([N:20]1[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[N:22]=[C:21]1SC)[CH3:19].Cl>C(OCC)(=O)C.CN(C=O)C>[F:3][C:4]([F:16])([F:17])[C:5]1[CH:11]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:9]=[CH:8][C:6]=1[NH:7][C:21]1[N:20]([CH2:18][CH3:19])[C:25](=[O:26])[CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[N:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 6028562,4-Bis(trifluoromethyl)anilineHCID 18549213HCID 18549213, compound

Product 1

HCID 18549224HCID 18549224, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil, 0.45 g, 11.4 mmol) was added to DMF (5 ml) solution of 2,4-bis(trifluoromethyl)aniline (2.00 g, 8.73 mmol), followed by stirring for 30 minutes. Then, 3-ethyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (2.08 g, 8 .73 mmol) was added, followed by stirring at 60° C. for 2 hours. After completion of the reaction, 1 N hydrochloric acid (30 ml) and ethyl acetate (20 ml) were added to the reaction solution to separate the organic layer, and the resulting aqueous layer was extracted with ethyl acetate (50 ml). The organic layers were combined, washed with water (30 ml×2) and saturated brine (70 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. By purifying the thus obtained crude product by a silica gel column chromatography (hexane:ethyl acetate=9:1˜7:3), white solid of 2-{2,4-bis(trifluoromethyl)phenyl}amino-3-ethyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 33] was obtained.

Workup

  1. stirringby stirring at 60° C. for 2 hours
  2. additionwere added to the reaction solution
  3. customto separate the organic layer
  4. extractionthe resulting aqueous layer was extracted with ethyl acetate (50 ml)
  5. washwashed with water (30 ml×2) and saturated brine (70 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe resulting filtrate was concentrated under a reduced pressure
  9. customBy purifying the

Sources & evidence

ORD record
ord-1063b3b265254f8eb650272f7bd0427e
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

Loading…