5599-20-2

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• 50-01-1 guanidine hydrochloride 
• 107-12-0 propiononitrile 

Relevant academic research and scientific papers

METHOD FOR PRODUCING 2-AMINO-1,3,5-TRIAZINE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing 2-amino-4,6-di-substituted 1,3,5-triazine simply and under a mild condition. SOLUTION: Guanidine or a salt thereof is added to a mixture including a nitrile compound and a base and reacted therewith to produce 2-amino-4,6-di-substituted 1,3,5-triazine. Alternatively, a mixture (or a mixed liquid) including guanidine or a salt thereof and a solvent may be added to a mixture (or a mixed liquid) including a nitrile compound, a base and a solvent and reacted therewith. The base may be an alkali metal hydride, for example, sodium hydride. After completing the reaction, a step of depositing a deposit by adding a poor solvent to the reaction mixture and a step of separating the deposited deposit may be included. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

2-Amino-1,3,5-triazine chemistry: hydrogen-bond networks, Takemoto thiourea catalyst analogs, and olfactory mapping of a sweet-smelling triazine

Abstract The chemistry of 4,6-dialkyl-2-amino-1,3,5-triazines with bulky alkyl substituents was investigated and their use as building blocks for preparing chiral thiourea organocatalysts explored. Reaction of ammonia with 4,6-di-tert-butyl-2-chloro-1,3,5-triazine gave 4,6-di-tert-butyl-1,3,5-triazin-2-amine which formed extended hydrogen-bond networks in the solid state according to X-ray crystallography. Selected heterocyclic amines were converted to isothiocyanates, and the latter reacted with (S,S)-2-(dimethylamino)cyclohexylamine to give enantiopure 1-hetaryl-3-[2-(dimethylamino)cyclohexyl]thioureas, with hetaryl representing either 4,6-dimethyl-1,3-diazin-2-yl, 4,6-diisopropyl-1,3,5-triazin-2-yl, or 4,6-di-tert-butyl-1,3,5-triazin-2-yl groups. These compounds are structural analogs of Takemotos's chiral thiourea organocatalysts (1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea) with an aza-aryl instead of the 3,5-bis(trifluoromethyl)phenyl group. They feature a strong intramolecular N-H to N-1 hydrogen bond, as shown by X-ray crystallography of 1-(4,6-di-tert-butyl-1,3,5-triazin-2-yl)-3-[2-(dimethylamino)cyclohexyl]thiourea in the solid state and by 1H NMR spectroscopy of all derivatives in CDCl3 solution, which prevents them from acting as bifunctional organocatalyst. In the reaction of 4,6-di-tert-butyl-2-chloro-1,3,5-triazine with ammonia, 4,6-di-tert-butyl-2-ethoxy-1,3,5-triazine was identified as side-product displaying a mildly sweet, floral odor that is unusual for a 1,3,5-triazine. Analogs (>35) of 4,6-di-tert-butyl-2-ethoxy-1,3,5-triazine were prepared to define the important structural factors of the olfactophore.