Cyanamide → HCID 178512321, compound

HRID 1902235Notes

Reaction equation

HRID 1902235 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[NH:17])OC)[N:9]=1)[C:2]([NH2:4])=[NH:3].[N:18]#[C:19][NH2:20]>CO>[C:19]([NH:20][C:14](=[NH:17])[CH2:13][CH2:12][CH2:11][CH2:10][C:8]1[N:9]=[C:5]([NH:1][C:2]([NH2:4])=[NH:3])[S:6][CH:7]=1)#[N:18]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 178496789HCID 178496789, compound

Product 1

HCID 178512321HCID 178512321, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 10 ml of methanol solution of 2.5 g of methyl 5-(2-guanidinothiazol-4-yl)pentanoimidate was added 0.6 g cyanamide, and the solution was stirred at room temperature for 1.5 hour. The solvent was distilled off, and to the residue was added 10 ml of acetone. The precipitated crystals were filtered off and the product was purified by using dimethylformamide-water. The purified product was dissolved in a mixture of 0.7 ml of acetic acid, 8 ml of ethanol and 16 ml of water, to the solution 11.6 ml of N-NaOH solution was added. The precipitated crystals were collected by filtration to provide 1.9 g of N-cyano-5-(2-guanidinothiazol-4-yl)pentanoamidine.

Workup

  1. distillationThe solvent was distilled off
  2. additionto the residue was added 10 ml of acetone
  3. filtrationThe precipitated crystals were filtered off
  4. customthe product was purified
  5. dissolutionThe purified product was dissolved in a mixture of 0.7 ml of acetic acid, 8 ml of ethanol and 16 ml of water, to the solution 11.6 ml of N-NaOH solution
  6. additionwas added
  7. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-3e289c71f21f4bfb8880df2ed5fed70f
Source dataset
uspto-grants-1982_12
Patent number
US04362736

Reaction notes

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