Diethyl Ether → HCID 178469093, compound

HRID 2052165Notes

Reaction equation

HRID 2052165 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)=[O:12])=[CH:5][CH:4]=1.[N:25]#[C:26][NH2:27].C(OCC)C>C(O)C>[ClH:1].[NH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)=[O:12])=[CH:7][CH:8]=1)[C:26]([NH2:27])=[NH:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9864CyanamideHCID 20378886HCID 20378886, compound

Product 1

HCID 178469093HCID 178469093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 200 ml of ethanol were dissolved 28.6 g of the p-ethoxycarbonylphenyl β-(p-aminophenyl)-propionate hydrochloride obtained and 4.2 g of cyanamide, and the solution was subjected to reaction at 70° C. for 5 hours. After the reaction, the solvent was removed by distillation under reduced pressure to obtain an oily product, to which a mixture consisting of ethanol and diethyl ether was added and the solution was cooled, upon which crystals precipitated. The crystals were collected by filtration and recrystallized from an ethanol-diethyl ether mixture to obtain p-ethoxycarbonylphenyl β-(p-guanidinophenyl)propionate hydrochloride in the form of colorless crystals. Yield: 25.1 g (78%); melting point: 125°-127° C.; IR (cm-1): 3500-2550, 1750, 1708, 1670, 1599; MS: M+= m/e 355 (M.W. - HCl).

Workup

  1. customobtained
  2. customAfter the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. customto obtain an oily product
  5. additionwas added
  6. temperaturethe solution was cooled, upon which crystals
  7. customprecipitated
  8. filtrationThe crystals were collected by filtration
  9. customrecrystallized from an ethanol-diethyl ether mixture

Sources & evidence

ORD record
ord-868098a077504b33ae39c74fbf58b9a9
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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