Potassium Carbonate → N,N'-bis(2-chloro-5-thiazolylmethyl)-N"-nitroguanidine

HRID 1275363Notes

Reaction equation

HRID 1275363 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9](=[N:12][N+:13]([O-:15])=[O:14])SC)=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[S:24][C:25]([CH2:28][NH2:29])=[CH:26][N:27]=1>C(#N)C>[Cl:22][C:23]1[S:24][C:25]([CH2:28][NH:29][C:9]([NH:8][CH2:7][C:4]2[S:3][C:2]([Cl:1])=[N:6][CH:5]=2)=[N:12][N+:13]([O-:15])=[O:14])=[CH:26][N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 101541292-Chloro-5-aminomethylthiazoleHCID 136331499N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea

Product 1

HCID 135827986N,N'-bis(2-chloro-5-thiazolylmethyl)-N"-nitroguanidineYield 13.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1 g N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea, 560 mg potassium carbonate, 400 mg cuprous chloride and 12 ml acetonitrile was added 610 mg of 2-chloro-5-(aminomethyl)thiazole and the mixture was stirred for 1 hour under reflux. Thereafter, the reaction mixture was concentrated, then water was added to the resultant solids, followed by stirring thoroughly. Thereafter, the solids were collected by filtration and purified by column chromatography [eluent: dichloromethane-methanol (10:1)] to afford 191 mg of N,N'-bis(2-chloro-5-thiazolylmethyl)-N"-nitroguanidine (compound No.39) as a white powder, mp 217-218° C.

Workup

  1. temperatureunder reflux
  2. concentrationThereafter, the reaction mixture was concentrated
  3. additionwater was added to the resultant solids
  4. stirringby stirring thoroughly
  5. filtrationThereafter, the solids were collected by filtration
  6. custompurified by column chromatography [eluent: dichloromethane-methanol (10:1)]

Sources & evidence

ORD record
ord-ec03cfea332e4b47aea7ffbfb6603369
Source dataset
uspto-grants-2000_12
Patent number
US06160126

Reaction notes

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