Ethanol → HCID 178468275, compound

HRID 67986Notes

Reaction equation

HRID 67986 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].[CH2:15]([OH:17])[CH3:16]>C(OCC)(=O)C>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:5](=[N:1][C:2]#[N:3])[O:17][CH2:15][CH3:16])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 702Ethanol3×HCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178468275HCID 178468275, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of diethyl (N-cyanoimido)carbonate (1.59 g.) in ethanol (15 ml.) at room temperature was added a solution of 2-guanidino-4-[(2-aminoethyl)thiomethyl]thiazole (2.58 g.) in ethanol (25 ml.) over 15 minutes with sufficient cooling to maintain the temperature at about 20° C. The solution was stirred at room temperature for a further 30 minutes and then more diethyl (N-cyanoimido)carbonate (0.318 g.) in ethanol (3 ml.) was added. The solution was stirred at room temperature for 15 minutes and then evaporated to dryness under reduced pressure to give a pale yellow paste. This residue was dissolved in ethyl acetate (20 ml.) and the solution was washed with water (20 ml., 2×10 ml.) then dried (magnesium sulphate) and evaporated under reduced pressure to give 2-guanidino-4-[2-(3-cyano-2-ethylisoureido)ethylthiomethyl]thiazole containing a small amount of ethyl acetate. The n.m.r. spectrum in CDCl3 using tetramethylsilane as internal standard had the following resonances (δ): 6.5 (5H, very broad); 6.4 (1H, singlet); 4-4.5 (obscured by ethyl acetate); 3.6 (2H, singlet); 3.4 (2H, multiplet); 2.7 (2H, multiplet); 2.0 (ethyl acetate); 1.2-1.5 (obscured by ethyl acetate).

Workup

  1. temperaturewith sufficient cooling
  2. stirringThe solution was stirred at room temperature for 15 minutes
  3. customevaporated to dryness under reduced pressure
  4. customto give a pale yellow paste
  5. washthe solution was washed with water (20 ml., 2×10 ml.)
  6. dry with materialthen dried (magnesium sulphate)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d76f7c92900446cf875c5146811e926b
Source dataset
uspto-grants-1982_08
Patent number
US04347370

Reaction notes

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