Acetonitrile → 1-(2-Methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one

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Reaction Steps

To a magnetically stirred suspension of 9.72 g. (40 mmol) of 1-(2'-methylphenyl)-3-methylamidinourea hydrochloride in 30 ml. of CH3CN is added 9.52 g. (80 ml.) of N,N-dimethylformamide dimethylacetal. After the mixture is further diluted with 25 ml. CH3CN and stirred for 5 minutes all of the solid is dissolved. TLC (3% NH4OH) shows a new spot; about equal in size to a spot in starting material; (EtoAc/MeOH; 9:1) shows mostly a new spot. The solution is refluxed for 2 hours. The reaction mixture is allowed to cool to ambient temperature. The reaction mixture is then poured into CHCl3 /H2O and separated. The aqueous layer is extracted with CHCl3 (for a total of 3×50 ml.). The organic layers are combined and washed with H2O (2×50 ml.). The aqueous layers are combined and back extracted with CHCl3 (1×50 ml.). All organic layers are combined, dried, filtered and concentrated in vacuo to yield the product which is recrystallized from absolute EtOH, filtered and washed with cold absolute EtOH and air-dried. The product is 1-(2'-methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one, melting point 191.5°-192.5° C.

Provenance & Evidence