Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 4-acetyloxycinnamate

HRID 1981444Notes

Reaction equation

HRID 1981444 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:36]1[CH:41]=[CH:40][C:39]([C:42](=[NH:44])[NH2:43])=[CH:38][C:37]=1[C:45](=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(=O)=O>N1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([O:13][C:36]2[CH:41]=[CH:40][C:39]([C:42](=[NH:43])[NH2:44])=[CH:38][C:37]=2[C:45](=[O:52])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 85857Cinnamic acid, p-hydroxy-, acetateHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Product 1

HCID 537773094-Amidino-2-benzoylphenyl 4-acetyloxycinnamateYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 3.1 g of 4-acetyloxycinnamic acid and 50 ml of dried pyridine, while being cooled in ice, was added 3.7 g of DCC. To the mixture, after having been stirred for 30 minutes, was added 5.0 g of 4-amidino-2-benzoylphenol methanesulfonate. The mixture was stirred overnight at room temperature. The insolubles precipitated from the reaction mixture were collected by filtration and mixed with DMF. Ethyl ether was added to the supernatant to precipitate an insoluble substance which was recrystallized from ethanol, yielding 4.7 g of colorless crystals of 4-amidino-2-benzoylphenyl 4-acetyloxycinnamate methanesulfonate.

Workup

  1. temperaturewhile being cooled in ice
  2. stirringThe mixture was stirred overnight at room temperature
  3. customThe insolubles precipitated from the reaction mixture
  4. filtrationwere collected by filtration
  5. additionmixed with DMF
  6. additionEthyl ether was added to the supernatant
  7. customto precipitate an insoluble substance which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-8bdb58005ec542978583bf02e67be454
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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