Acetic Anhydride → HCID 19097278, compound

HRID 486010Notes

Reaction equation

HRID 486010 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]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([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]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:3]=1)(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 19097279HCID 19097279, compound

Product 1

HCID 19097278HCID 19097278, compound

Procedure

A solution of 7-amino-2-(2-furyl)-5-[4-methoxyphenyl][1,2,4]triazolo[1,5-a][1,3,5]triazine (0.23 g) in acetic anhydride (10 ml) was heated on the steam-bath for 18 hours. The solvent was then evaporated in vacuo and the residue was purified by chromatography on silica-gel eluting with dichloromethane containing ethyl acetate (5% v/v). The solid obtained from the chromatography was crystallised from ethanol and gave 7-acetylamino-2-(2-furyl)-5-[4-methoxyphenyl][1,2,4]triazolo[1,5-a][1,3,5]triazine m.p. 243°-6° C.; microanalysis, found: C, 58.0; H, 4.0; N, 23.9% C17H14N6O3 requires C, 58.3; H, 4.0; N, 24.0%; NMR 2.50 (s, NHCOCH3), 3.87 (s, 3H, CH3O), 6.75 (d of d, 1H, furyl-4H), 7.12 and 8.42 (A2B2 pattern, 4H, phenyl-H), 7.32 (d, 1H, furyl-3H), 7.98 (d, 1H, furyl-5H) and 11.42 (s, H, NHCOCH); m/e 351 (M+H)+.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue was purified by chromatography on silica-gel
  3. washeluting with dichloromethane
  4. additioncontaining ethyl acetate (5% v/v)
  5. customThe solid obtained from the chromatography
  6. customwas crystallised from ethanol

Sources & evidence

ORD record
ord-e4084a8218dd4fde999e4a478769de40
Source dataset
uspto-grants-1994_03
Patent number
US05290776

Reaction notes

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