Ethanol → 1-Methyl-N5-[3-[3-(aminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

HRID 2058738Notes

Reaction equation

HRID 2058738 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH:15]=[CH:16][CH:17]=2)[N:4]([CH3:30])[N:3]=1.O.NN.C(O)C>>[CH3:30][N:4]1[C:5]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:19])[CH:13]=2)=[N:6][C:2]([NH2:1])=[N:3]1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 212975782-[[3-[3-[(3-amino-1-methyl-1H-1,2,4-triazol-5-yl)amino]propoxy]phenyl]methyl]-1H-isoindole-1,3-(2H)-dione

Product 1

HCID 544903661-Methyl-N5-[3-[3-(aminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamineYield 71.7%

Procedure

A solution of 2-[[3-[3-[(3-amino-1-methyl-1H-1,2,4-triazol-5-yl)amino]propoxy]phenyl]methyl]-1H-isoindole-1,3-(2H)-dione (1.62 g) and hydrazine hydrate (0.22 g) in ethanol (10 mol) was heated at reflux for 1.5 h. The solvent was evaporated and the residue was dissolved in dilute hydrochloric acid and filtered. The filtrate was basified with sodium carbonate, evaporated to dryness and extracted with hot isopropanol to give an oil which was purified by column chromatography using methanol/0.88 ammonia 79:1 an eluant to give the title compound as a crystalline solid (0.79 g) TLC silica, methanol/0.88 ammonia 79:1 Rf 0.5 NMR (d4MeOH) 2.77 t (1H); 3.0-3.3 m (3H); 5.95 t (2H); 6.30 s (2H); 6.57 q (2H); 6.65 s (3H); 7.95 m (2H).

Workup

  1. temperatureat reflux for 1.5 h
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in dilute hydrochloric acid
  4. filtrationfiltered
  5. customevaporated to dryness
  6. extractionextracted with hot isopropanol
  7. customto give an oil which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-44219833148d47bba2d5bcebcfd87434
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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