Dimethyl N-cyanodithioiminocarbonate → HCID 11776764, compound

HRID 5820

Reaction equation

HRID 5820 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

HCID 11776764HCID 11776764, compoundYield 20.3%

Conditions

Temperature
170 °C

Procedure

An intimate mixture of 3-amino-5-(2-furyl)-1,2,4-triazole (33.0 g) and dimethyl N-cyanodithioiminocarbonate (33.0 g) was heated at 170° C. for 1 hour, under a slow stream of argon. After cooling, the resulting solid was purified by column chromatography on silica (600 g) eluting with an increasing amount of ethyl acetate in dichloromethane (5-10% v/v) to give 7-amino-2-(2-furyl)-5-methylthio-[1,2,4]triazolo[1,5-a][1,3,5]triazine as a colourless solid (11.1 g), essentially pure by TLC, which was used without further purification. [A small amount of the above solid was recrystallised from ethanol to give, crystals, m.p. 238°-240° C.; microanalysis, found: C,44.0; H,3.3; N,33.7; C9H8N6SO. 0.05C2H5OH requires C,43.6; H,3.3; N,33.6; NMR 1.05 and 3.4 (t+q, ethanol of crystallisation), 2.5 (s, 3H, CH3S-- ), 6.7(dd, 1H, furyl-4H), 7.2(d, 1H, furyl-3H), 7.7(d, 1H, furyl-5H) 8.7-9.0(br d, 2H, NH2); m/e 248 (M+).

Workup

  1. temperatureAfter cooling
  2. customthe resulting solid was purified by column chromatography on silica (600 g)
  3. washeluting with an increasing amount of ethyl acetate in dichloromethane (5-10% v/v)

Sources & evidence

ORD record
ord-263a470489eb4f31aa2b7a9416d2c743
Source dataset
uspto-grants-1993_09
Patent number
US05246932

Linked notes

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