Dicyclohexylcarbodiimide → alpha-Cyano-phenylacetic acid pentafluorophenyl ester

HRID 1980230Notes

Reaction equation

HRID 1980230 reaction equation
[C:1]([CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5])#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.[F:28][C:29]1[C:34](O)=[C:33]([F:36])[C:32]([F:37])=[C:31]([F:38])[C:30]=1[F:39]>ClCCl>[F:28][C:29]1[C:34]([O:5][C:4](=[O:6])[CH:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1]#[N:2])=[C:33]([F:36])[C:32]([F:37])=[C:31]([F:38])[C:30]=1[F:39]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 26403alpha-Cyanobenzeneacetic acid

Product 1

HCID 20402416alpha-Cyano-phenylacetic acid pentafluorophenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8 g. (0.05 moles) of α-cyano-phenylacetic acid are dissolved in dichloromethane. Under mild heating 10.3 g. (0.05 moles) of dicyclohexylcarbodiimide and 0.2 g. (0.05 moles) of pentafluorophenol dissolved in 50 ml. of dichloromethane are added dropwise. The mixture is stirred for 4 hours at 30° to 35° C. It is cooled, and the precipitated dicyclohexylurea is filtered. The substance on the filter is washed twice with 10 ml. of dichloromethane. The combined organic layers are evaporated while petrolether is added. The crystalline ester is precipitated from petrolether.

Workup

  1. temperatureUnder mild heating 10.3 g
  2. temperatureIt is cooled
  3. filtrationthe precipitated dicyclohexylurea is filtered
  4. washThe substance on the filter is washed twice with 10 ml
  5. customThe combined organic layers are evaporated while petrolether
  6. additionis added
  7. customThe crystalline ester is precipitated from petrolether

Sources & evidence

ORD record
ord-0361bef0518044dda4bf52a0a9465b72
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Reaction notes

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