Cyanamide → HCID 178439144, compound

HRID 2052161Notes

Reaction equation

HRID 2052161 reaction equation
Cl.[CH3:2][CH:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[C:4]([O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=[O:5].[N:22]#[C:23][NH2:24]>C(O)C>[ClH:13].[CH3:2][CH:3]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:23]([NH2:24])=[NH:22])[CH:16]=1)[C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 20378935HCID 20378935, compound

Product 1

HCID 178439144HCID 178439144, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 ml of ethanol were dissolved 23.0 g of the p-chlorophenyl α-methyl-β-(m-aminophenyl)-propionate hydrochloride thus obtained and 4.2 g 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 p-chlorophenyl α-methyl-β-(m-guanidinophenyl)-propionate hydrochloride in the form of an oily matter. This compound 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 p-chlorophenyl α-methyl-β-(m-guanidinophenyl)-propionate carbonate. Yield: 19.4 g (70%); melting point: 87°-90° C.; IR (cm-1); 3500-2500, 1748, 1660, 1490; MS: M+ =m/e 331 (M.W. - H2CO3).

Workup

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

Sources & evidence

ORD record
ord-241e9e1e01bd47e9b0b1f70014e9a6ce
Source dataset
uspto-grants-1980_01
Patent number
US04182897

Reaction notes

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