HCID 178434111, compound → HCID 178434108, compound

HRID 1971461Notes

Reaction equation

HRID 1971461 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([NH:7][C:8]([NH:10]C(=O)C2C=CC=CC=2)=[S:9])=[N:5][N:6]=1>[OH-].[Na+]>[CH3:1][C:2]1[NH:3][C:4]([NH:7][C:8]([NH2:10])=[S:9])=[N:5][N:6]=1

Participants

3

Reactant 1

HCID 178434111HCID 178434111, compound

Product 1

HCID 178434108HCID 178434108, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The saponification of N-{[(5-methyl-4H-1,2,4-triazole-3-yl)amino]carbonothioyl}-benzamide in methanolic sodium hydroxide solution, could be performed even at room temperature. The N-(5-methyl-4H-1,2,4-triazole-3-yl)thiourea formed was alkylated with methyl iodide at room temperature and the resulting methyl N-(5-methyl-4H-1,2,4-triazole-3-yl)imidothiocarbamate was liberated by extraction of the organic phase with 1 N NaOH. Finally, the methyl N-(5-methyl-4H-1,2,4-triazole-3-yl)imidothiocarbamate was brought to reaction with 2,6-dimethoxybenzylamine in ethanol at 130° C. in the microwave (100 Watt) and the N-(2,6-dimethoxybenzyl)-N′-(5-methyl-4H-1,2,4-triazole-3-yl)guanidine was isolated following chromatographic purification on preparative HPLC (Merck: Chromolith RP-18E, 100-25; eluent water/acetonitrile/0.1 molar acetic acid).

Workup

  1. customcould be performed even at room temperature

Sources & evidence

ORD record
ord-17e5c6a3e11c451689892db55578a2a6
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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