Cyanamide → N-[4-(4-guanidinophenyl)butanoyl]thiazolidine hydrochloride

HRID 1614563Notes

Reaction equation

HRID 1614563 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH2:18][CH2:17][S:16][CH2:15]2)=[O:13])=[CH:5][CH:4]=1.[N:19]#[C:20][NH2:21]>C(O)C>[ClH:1].[NH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([N:14]2[CH2:18][CH2:17][S:16][CH2:15]2)=[O:13])=[CH:7][CH:8]=1)[C:20]([NH2:21])=[NH:19]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 14822258HCID 14822258, compound

Product 1

HCID 178479369N-[4-(4-guanidinophenyl)butanoyl]thiazolidine hydrochlorideYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

1 mmol of N-[4-(4-aminophenyl)butanoyl]thiazolidine hydrochloride prepared in Example 20 and 1 mmol of cyanamide were dissolved with 5 ml of anhydrous ethanol. The solution was stirred under heating at 70° C. for 4 hours. The reaction mixture was concentrated under reduced pressure to obtain a crystalline residue, which was recrystallized from an ethanol-ether mixed solvent to obtain 210 mg of colorless crystals of N-[4-(4-guanidinophenyl)butanoyl]thiazolidine hydrochloride (yield: 64%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto obtain a crystalline residue, which
  3. customwas recrystallized from an ethanol-ether mixed solvent

Sources & evidence

ORD record
ord-5a92df905a30436689925b635f8ae8d4
Source dataset
uspto-grants-1993_03
Patent number
US05198450

Reaction notes

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