Dicyclohexylcarbodiimide → HCID 13313792, compound

HRID 1380424Notes

Reaction equation

HRID 1380424 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH2:16]([NH:23][C:24]([NH:26][CH2:27][CH:28]([C:33]([OH:35])=O)[C:29]([F:32])([F:31])[F:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:23]1[C:33](=[O:35])[CH:28]([C:29]([F:32])([F:31])[F:30])[CH2:27][NH:26][C:24]1=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 13313789HCID 13313789, compound

Product 1

HCID 13313792HCID 13313792, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of DCC (430 mg; 2.1 mmoles) in DMF (1 ml) was added dropwise to a solution of 1-benzyl-3-(2-hydroxycarbonyl-3,3,3-trifluoropropyl)urea (580 mg; 2.0 mmoles) obtained above in DMF (2 ml). One hour later, 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 468 mg (yield: 86%) of 3-benzyl-5-trifluoromethyl-5,6-dihydrouracil.

Workup

  1. filtrationOne hour later, the precipitated solid was filtered off
  2. washwashed with ethyl acetate
  3. customThe solvents were evaporated under reduced pressure from the combined filtrates
  4. customThe residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:1)

Sources & evidence

ORD record
ord-1759a2308ee94699bac073b70f7f2d14
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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