Dimethyl N-cyanodithioiminocarbonate → HCID 11776764, Verbindung

HRID 486009

Reaktionsgleichung

Reaktionsgleichung von HRID 486009
[NH2:1][C:2]1[N:6]=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[NH:4][N:3]=1.[CH3:12][S:13][C:14](SC)=[N:15][C:16]#[N:17]>>[NH2:17][C:16]1[N:3]2[N:4]=[C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)[N:6]=[C:2]2[N:1]=[C:14]([S:13][CH3:12])[N:15]=1

Komponenten

3

Edukt 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 100347805-(2-Furyl)-4h-1,2,4-triazol-3-amine

Produkt 1

HCID 11776764HCID 11776764, Verbindung

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

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+).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe resulting solid was triturated with methanol
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-cceb05e903644540b960199bb38cdf2f
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290776

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