Benzylurea → HCID 13313792, compound

HRID 1380417Notes

Reaction equation

HRID 1380417 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[CH2:10]([NH:17][C:18]([NH2:20])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH2:10]([N:17]1[C:4](=[O:5])[CH:3]([C:2]([F:9])([F:8])[F:1])[CH2:7][NH:20][C:18]1=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 10853BenzylureaHCID 10868DicyclohexylcarbodiimideHCID 5876942-(Trifluoromethyl)acrylic acid

Product 1

HCID 13313792HCID 13313792, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and benzylurea (796 mg; 5.3 mmoles) in DMF (5 ml) was heated at 90° C. with stirring for 5 hours. After the reaction mixture was cooled to 0° C., a solution of DCC (1.13 g; 5.5 mmoles) in DMF (3 ml) was added dropwise. The mixture was stirred for 1 hour, and the precipitated solid was filtered off and washed with ethyl acetate. The solvents were evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:1) to give 979 mg (yield: 72%) of 3-benzyl-5-trifluoromethyl-5,6-dihydrouracil. m.p.: 129.2°-129.7° C.

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringThe mixture was stirred for 1 hour
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with ethyl acetate
  5. customThe solvents were evaporated under reduced pressure from the combined filtrates
  6. customThe residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:1)

Sources & evidence

ORD record
ord-7208f5f484684aafb568a991c281241a
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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