Hydrochloric Acid → HCID 18549202, compound

HRID 1266197Notes

Reaction equation

HRID 1266197 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[C:5]=1[NH2:6].[CH3:16][N:17]1[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=[C:18]1SC.Cl>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C=O)C>[Cl:3][C:4]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]([Cl:15])[C:5]=1[NH:6][C:18]1[N:17]([CH3:16])[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[N:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1410944-Amino-3,5-dichlorobenzotrifluorideHCID 1486660HCID 1486660, compound

Product 1

HCID 18549202HCID 18549202, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil, 0.31 g, 7.65 mmol) was added to DMF (5 ml) solution of 2,6-dichloro-4-trifluoromethylaniline (0.80 g, 3.48 mmol), followed by stirring for 30 minutes. Then, 3-methyl-2-methylthio-6-trifluoromethyl-4(3H)-pyrimidinone (0.70 g, 3.13 mmol) was added, followed by stirring at 50° C. for 8 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 recrystallizing the thus obtained crude product from toluene and then from chloroform, white solid of 2-(2,6-dichloro-4-trifluoromethylphenyl)amino-3-methyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 28] was obtained.

Workup

  1. stirringby stirring at 50° C. for 8 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 recrystallizing the
  10. customthus obtained crude product from toluene

Sources & evidence

ORD record
ord-59858b153f4f4248939b5c5db70ab0f9
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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