Acetic Anhydride → HCID 15730044, compound

HRID 1707999Notes

Reaction equation

HRID 1707999 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([NH:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:3]=1)(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 3071852(1,2,4)Triazolo(1,5-a)triazin-7-amine, 2-(2-furanyl)-5-phenoxy-

Product 1

HCID 15730044HCID 15730044, compound

Procedure

A solution of 7-amino-2-(2-furyl)-5-phenoxy-[1,2,4]triazolo[1,5-a][1,3,5]triazine (950 mg) in acetic anhydride was heated under reflux for 1.5 hours. The solvent was then evaporated in vacuo and the residue was purified by chromatography on silica eluting with dichloromethane containing ethyl acetate (5% v/v). The amorphous solid thereby obtained was crystallised from toluene to give 7-acetylamino-2-(2-furyl)-5-phenoxy-[1,2,4]-triazolo[1,5-a][1,3,5]triazine as colourless prisms, m.p. 168°-170° C.; microanalysis, found; C, 60.9; H, 4.2; N, 22.6%; C16H12N6O3 0.45 C7H8 requires: C, 60.9; H, 4.1; N, 22.3%; NMR 2.3 (s, 3H equivalent, toluene CH3), 2.35 (s, 3H, CH3CO), 6.7 (q, 1H, furyl-4H), 7.1-7.6 (complex, 6H, furyl-3H+ phenyl-H+toluene), 7.95(d, 1H, furyl-5H), 11.5 (broad s, 1H, NH); m/e 336 (M+).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customThe solvent was then evaporated in vacuo
  3. customthe residue was purified by chromatography on silica eluting with dichloromethane
  4. additioncontaining ethyl acetate (5% v/v)
  5. customThe amorphous solid thereby obtained
  6. customwas crystallised from toluene

Sources & evidence

ORD record
ord-4a918130928345c4830ad7c493fca3a7
Source dataset
uspto-grants-1994_10
Patent number
US05356894

Reaction notes

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