Dicyclohexylcarbodiimide → HCID 13313793, compound

HRID 1380422Notes

Reaction equation

HRID 1380422 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[OH:16][C:17]([CH:19]([C:31]([F:34])([F:33])[F:32])[CH2:20][NH:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23])=O>CN(C=O)C>[C:25]1([N:24]2[C:17](=[O:16])[CH:19]([C:31]([F:34])([F:33])[F:32])[CH2:20][NH:21][C:22]2=[O:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 13313790HCID 13313790, compound

Product 1

HCID 13313793HCID 13313793, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of DCC (206 mg; 1.0 mmole) in DMF (0.5 ml) was added dropwise to a solution of 1-(2-hydroxycarbonyl-3,3,3-trifluoropropyl)-3-phenylurea (276 mg; 1.0 mmole) obtained above in DMF (1 ml), and the mixture was stirred for 1 hour. 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=1:3) to give 120 mg (yield: 47%) of 3-phenyl-5-trifluoromethyl-5,6-dihydrouracil. m.p.: 215°-216° C.

Workup

  1. filtrationThe 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=1:3)

Sources & evidence

ORD record
ord-c8777efc03214e22a37f37770dbc98b5
Source dataset
uspto-grants-1986_04
Patent number
US04581452

Reaction notes

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