Cyanamide → HCID 178439143, compound

HRID 2052164Notes

Reaction equation

HRID 2052164 reaction equation
[ClH:1].[CH3:2][CH:3]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=1)[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[N:21]#[C:22][NH2:23]>C(O)C>[ClH:1].[CH3:2][CH:3]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:22]([NH2:23])=[NH:21])[CH:15]=1)[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 20378862HCID 20378862, compound

Product 1

HCID 178439143HCID 178439143, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 ml of ethanol were dissolved 24.3 g of the phenyl α-methyl-β-(m-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 phenyl α-methyl-β-(m-guanidinophenyl)-propionate hydrochloride in the form of an oily matter. This was dissolved in 50 ml of ethanol and then added to saturated aqueous NaHCO3 solution, upon which colorless crystals precipitated. The crystals were collected by filtration and washed with water and acetone, to obtain phenyl α-methyl-β-(m-guanidinophenyl)-propionate carbonate. Yield: 22.6 g (75%); melting point: 97°-98° C.; IR (cm-1): 3500-2500, 1745, 1682, 1625; MS: M+= m/e 297 (M.W.-H2CO3).

Workup

  1. customobtained
  2. customAfter the reaction
  3. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-6ad6e39adf3f4748a2aec402da1d5cf1
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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