Dicyclohexylcarbodiimide → HCID 54573561, compound

HRID 1980231Notes

Reaction equation

HRID 1980231 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])#[N:2].[F:14][C:15]1[C:20](O)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[F:14][C:15]1[C:20]([O:5][C:4](=[O:6])[C:3]([C:1]#[N:2])=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 705342-Cyano-3-phenylprop-2-enoic acid

Product 1

HCID 54573561HCID 54573561, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9.0 g. (0.05 moles) of α-cyano-β-phenyl-acrylic acid are suspended in 200 ml. of dichloromethane and 9.2 g. (0.05 moles) of pentafluorophenol and 10.02 g. (0.05 moles) of dicyclohexylcarbodiimide in 100 ml. dichloromethane are added. The mixture is heated for 5 hours under reflux, cooled, the precipitated dicyclohexyl urea is filtered off. The solution is washed with 20 ml. of 2n hydrochloric acid and three times with water, dried over magnesium sulfate, evaporated and the residual oily substance is recrystallized from petrolether.

Workup

  1. temperatureThe mixture is heated for 5 hours
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationthe precipitated dicyclohexyl urea is filtered off
  5. washThe solution is washed with 20 ml
  6. dry with materialof 2n hydrochloric acid and three times with water, dried over magnesium sulfate
  7. customevaporated
  8. customthe residual oily substance is recrystallized from petrolether

Sources & evidence

ORD record
ord-2fdbb87a6bca4815a59380de8d0776d4
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Reaction notes

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