Hydrazine → 5-[(4-Fluorophenyl)methyl]-4H-1,2,4-triazole-3,4-diamine

HRID 1822893Notes

Reaction equation

HRID 1822893 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2O[C:10]([NH2:12])=[N:9][N:8]=2)=[CH:4][CH:3]=1.[NH2:15][NH2:16]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:15]([NH2:16])[C:10]([NH2:12])=[N:9][N:8]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 219193195-[(4-Fluorophenyl)methyl]-1,3,4-oxadiazol-2-amine

Product 1

HCID 219193225-[(4-Fluorophenyl)methyl]-4H-1,2,4-triazole-3,4-diamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 5-(4-fluoro-benzyl)-[1,3,4]oxadiazol-2-ylamine 10.182 g (52.7 mmol), water 80 mL and anhydrous hydrazine 20 mL was refluxed under nitrogen on an oil bath (190-200° C.) for 23 hours. The mixture was cooled and allowed to crystallize at room temperature under nitrogen overnight. The precipitated product was collected by filtration, washed with ice-cold water (10 mL) and dried on high vacuum. The crude product was re-crystallized from water 60 mL (reflux under nitrogen, than to +4° C. in a refrigerator overnight). The product was filtered, washed with ice-cold water and dried on high vacuum.

Workup

  1. temperatureThe mixture was cooled
  2. customto crystallize at room temperature under nitrogen overnight
  3. filtrationThe precipitated product was collected by filtration
  4. washwashed with ice-cold water (10 mL)
  5. customdried on high vacuum
  6. customThe crude product was re-crystallized from water 60 mL (
  7. temperaturereflux under nitrogen, than to +4° C. in a refrigerator overnight)
  8. filtrationThe product was filtered
  9. washwashed with ice-cold water
  10. customdried on high vacuum

Sources & evidence

ORD record
ord-c49bb0db4d86438294f0252143e83318
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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