2-Chloro-5-aminomethylthiazole → N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

HRID 373795

Reaction equation

HRID 373795 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH2:8])=[CH:5][N:6]=1.CS[C:11](=[N:14][N+:15]([O-:17])=[O:16])[NH:12][CH3:13]>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:11]([NH:12][CH3:13])=[N:14][N+:15]([O-:17])=[O:16])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 101541292-Chloro-5-aminomethylthiazoleHCID 1362270171,2-Dimethyl-3-nitroisothiourea

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidineYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.48 g of 2-chloro-5-thiazolemethanamine, 0.31 g of S-methyl-N-methyl-N'-nitroisothiourea prepared by the method described in the Journal of Medical Chemistry., 1977, Vol. 20, No. 7, P. 905 and 3 ml of ethanol was heated under reflux for 6 hours. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Solvent: Chloroform/Methanol =20/1) to obtain 0.37 g of the title compound as crystals. This compound is No. 8 in Table 1. m.p.: 151.0°-153.0° C.

Workup

  1. customprepared by the method
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Solvent: Chloroform/Methanol =20/1)

Sources & evidence

ORD record
ord-49f0d7f98ad84f98adfa15b26181d2ec
Source dataset
uspto-grants-1992_11
Patent number
US05166164

Linked notes

Loading…