Ethyl 4,4,4-trifluoro-3-oxo-2-phenylbutanoate → 6-Trifluoromethyl-3-[1-methyl-1-(3,5-dichlorophenyl)ethyl]-5-phenyl-2,3-dihydro-4H-1,3-oxazin-4-one

HRID 1939147Notes

Reaction equation

HRID 1939147 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8]CC)=O)=[O:4].[CH2:19]=[N:20][C:21]([CH3:31])([C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1)[CH3:22]>C1(C)C(C)=CC=CC=1>[F:18][C:2]([F:1])([F:17])[C:3]1[O:4][CH2:19][N:20]([C:21]([CH3:31])([C:23]2[CH:24]=[C:25]([Cl:30])[CH:26]=[C:27]([Cl:29])[CH:28]=2)[CH3:22])[C:6](=[O:8])[C:5]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 13913997Ethyl 4,4,4-trifluoro-3-oxo-2-phenylbutanoateHCID 21223286N-methylene-1-methyl-1-(3,5-dichlorophenyl)ethylamine

Product 1

HCID 212232766-Trifluoromethyl-3-[1-methyl-1-(3,5-dichlorophenyl)ethyl]-5-phenyl-2,3-dihydro-4H-1,3-oxazin-4-oneYield 84%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl 2-trifluoroacetyl-2-phenylacetate (1.30 g) and N-methylene-1-methyl-1-(3,5-dichlorophenyl)ethylamine (1.19 g) were mixed, and xylene (10 ml) was added thereto. The mixture was allowed to react by refluxing for 30 minutes. The solvent was removed by evaporation, and the crude product was recrystallized from a mixture of hexane and ethyl acetate to afford the captioned compound (1.80 g, yield 84%).

Workup

  1. customto react
  2. temperatureby refluxing for 30 minutes
  3. customThe solvent was removed by evaporation
  4. customthe crude product was recrystallized from a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-23118503df7048059f2b101b339f46a4
Source dataset
uspto-grants-1997_12
Patent number
US05696054

Reaction notes

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