Benzenamine, 2-chloro-5-(trifluoromethyl)- → HCID 18549197, compound

HRID 1266196Notes

Reaction equation

HRID 1266196 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1Cl.[CH2:13]([N:17]1[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=[C:18]1S(C)(=O)=O)[CH2:14][CH2:15][CH3:16].[Cl-:32].[NH4+]>CN(C=O)C.CCOCC.[H-].[Na+]>[CH2:13]([N:17]1[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=[C:18]1[NH:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([Cl:32])[CH:7]=1)[CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 3

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 18549225HCID 18549225, compound

Product 1

HCID 18549197HCID 18549197, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent2×

Procedure

3-Amino-4-chlorobenzotrifluoride (2.9 g, 12.7 mmol) was dissolved in DMF (30 ml), sodium hydride (60% in oil, 540 mg, 13.5 mmol) was added, followed by stirring at room temperature for 30 minutes. Then, 3-butyl-2-methylsulfonyl-6-trifluoromethyl-4(3H)-pyrimidinone (3.0 g, 11.7 mmol) was added, followed by stirring for 4 hours. After completion of the reaction, the reaction solution was diluted with ether (20 ml), excess sodium hydride was neutralized with saturated ammonium chloride aqueous solution, and then the organic layer was separated and the resulting aqueous layer was extracted with ether (15 ml×2). The organic layers were combined, washed with saturated brine and then dried over anhydrous sodium 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=10:1), 3-butyl-2-(3-chloro-5-trifluoromethylphenyl)amino-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 22] was obtained as colorless crystals.

Workup

  1. stirringby stirring for 4 hours
  2. customAfter completion of the reaction
  3. customthe organic layer was separated
  4. extractionthe resulting aqueous layer was extracted with ether (15 ml×2)
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe resulting filtrate was concentrated under a reduced pressure
  9. customBy purifying the
  10. customthus obtained crude product by a silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a3f8793ddab04dcda499d68e83c3da72
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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