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3-amino-5-(2-furyl)-[1,2,4]triazole

dimethyl N-cyanodithioiminocarbonate

→

7-amino-2-(2-furyl)-5-methylthio[1,2,4]triazolo[1,5-a][1,3,5]triazine

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후처리

1. 1
   온도After cooling
2. 2
   기타the resulting solid was triturated with methanol
3. 3
   여과filtered

실험 절차

An itimate mixture of 3-amino-5-(2-furyl)-[1,2,4]triazole (15 g) and dimethyl N-cyanodithioiminocarbonate (16 g) was heated at 170° C. for 50 minutes under a slow stream of argon. After cooling, the resulting solid was triturated with methanol and filtered to afford 7-amino-2-(2-furyl)-5-methylthio[1,2,4]triazolo[1,5-a][1,3,5]triazine as a yellow-green solid. The residue from the filtrate was chromatographed on silica gel, eluting with dichloromethane-methanol 97.5/2.5 v/v to give further 7-amino-2-(2-furyl)-5-methylthio[1,2,4]triazolo[1,5-a][1,3,5]triazine (4.4 g) followed by 5-amino-2-(2-furyl)-7-methylthio-[1,2,4]triazolo[1,5-a][1,3,5]triazine (2.2 g) as a yellow solid. A small amount of the above solid was crystallised from methanol and gave pale yellow needles, m.p. 254°-7° C.; microanalysis, found: C, 43.0; H, 3.5; N, 33.4; S 12.4%; C9H8N6OS (0.125)CH3OH requires: C, 43.4, H, 3.6; N, 33.3; S, 12.7%; NMR: 2.67 (s, 3H, CH3S), 6.68 (d of d, 1H, furyl-4H), 7.15 (d, 1H, furyl-3H); 7.68 (br s, 2H, NH2) and 7.89 (d, 1H, furyl-5H); m/e 248 (M+).

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