Diethyl Ether → HCID 178426886, compound

HRID 2052162Notes

Reaction equation

HRID 2052162 reaction equation
[ClH:1].[CH3:2][CH:3]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)[C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[O:5].[N:22]#[C:23][NH2:24].C(OCC)C>C(O)C>[ClH:1].[CH3:2][CH:3]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:23]([NH2:24])=[NH:22])=[CH:19][CH:20]=1)[C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9864CyanamideHCID 20378929HCID 20378929, compound

Product 1

HCID 178426886HCID 178426886, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In 200 ml of ethanol were dissolved 21.8 g of the p-methylphenyl α-methyl-β-(p-aminophenyl)-propionate hydrochloride obtained and 4.2 of cyanamide, and the resulting 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. A mixture of ethanol and diethyl ether was added thereto 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-methylphenyl α-methyl-β-(p-guanidinophenyl)propionate hydrochloride in the form of colorless crystals. Yield: 17.4 g (70%); melting point: 146°-148° C.; IR (cm-1): 3500-2550, 1748, 1653, 1631; MS: M+ =m/e 312 (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-d30e731c12874ba293abb3207e2af74c
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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