Dimethyl N-cyanodithioiminocarbonate → HCID 11776764, 화합물

HRID 1768909

반응식

HRID 1768909 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 11776764HCID 11776764, 화합물수율 20.3%

반응 조건

온도
170 °C

실험 절차

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 and gave, 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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-bef8a48253e64bae89cb879346510372
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380714

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