Phenylacetic Acid → HCID 86739853, compound

HRID 1154581Notes

Reaction equation

HRID 1154581 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:26][S:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]=[CH:38][C:39](=[NH:41])[NH2:40])=[CH:33][CH:32]=1)(=[O:29])=[O:28]>N1C=CC=CC=1>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[C:1]1([CH2:7][C:8]([O:10][C:31]2[CH:36]=[CH:35][C:34]([CH:37]=[CH:38][C:39](=[NH:40])[NH2:41])=[CH:33][CH:32]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 54417104HCID 54417104, compound

Product 1

HCID 86739853HCID 86739853, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.4 g of phenylacetic acid in 50 ml of dried pyridine, was added 3.1 g of DCC. After 30 minutes of stirring, 2.6 g of 4-(β-amidinoethenyl)phenol methanesulfonate was added to the mixture and stirred overnight. The insolubles were removed by filtration and ethyl ether was added to the filtrate to precipitate crystals. The crystals were collected by filtration and recrystallized from ethanol to obtain 1.5 g of 4-(β-amidinoethenyl)phenyl phenylacetate methanesulfonate.

Workup

  1. stirringstirred overnight
  2. customThe insolubles were removed by filtration and ethyl ether
  3. additionwas added to the filtrate
  4. customto precipitate crystals
  5. filtrationThe crystals were collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5c404dc0c5ad4154b6ed2058dab4935d
Source dataset
uspto-grants-1984_12
Patent number
US04490388

Reaction notes

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