Hydrazine → 4-[(4,5-Diamino-4H-1,2,4-triazol-3-yl)methyl]phenol

HRID 1822890Notes

Reaction equation

HRID 1822890 reaction equation
[NH2:1][C:2]1O[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[N:4][N:3]=1.[NH2:15][NH2:16]>O>[NH2:15][N:16]1[C:2]([NH2:1])=[N:3][N:4]=[C:5]1[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 219193154-[(5-Amino-1,3,4-oxadiazol-2-yl)methyl]phenol

Product 1

HCID 219193134-[(4,5-Diamino-4H-1,2,4-triazol-3-yl)methyl]phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 4-(5-amino-[1,3,4]oxadiazol-2-ylmethyl)-phenol 4.902 g (25.64 mmol), water 40 mL and anhydrous hydrazine 13 mL was refluxed on an oil bath (190° C.) for 18 hours. The mixture was cooled, allowed to crystallize at room temperature for 2 hours, then placed into a freezer (−20° C.) overnight (16 hrs). The precipitated product was collected by filtration, washed with chilled MeOH (−15° C.) and dried on high vacuum. The crude product was re-crystallized from water (80 mL, reflux to +4° C. overnight). Filtered, washed with ice-cold water and dried on high vacuum.

Workup

  1. temperatureThe mixture was cooled
  2. customto crystallize at room temperature for 2 hours
  3. customplaced into a freezer (−20° C.) overnight (16 hrs)
  4. filtrationThe precipitated product was collected by filtration
  5. washwashed with chilled MeOH (−15° C.)
  6. customdried on high vacuum
  7. customThe crude product was re-crystallized from water (80 mL, reflux to +4° C. overnight)
  8. filtrationFiltered
  9. washwashed with ice-cold water
  10. customdried on high vacuum

Sources & evidence

ORD record
ord-aeccf71ca57347498bb92e6833691b34
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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