1,2-Hydrazinedicarboxaldehyde → 4-phenyl-1H-1,2,3-triazole

HRID 1774360Notes

Reaction equation

HRID 1774360 reaction equation
[Br-].C1([N+:8]2[NH:9][N:10]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]CCCCCCCC)[CH:12]=2)C=CC=CC=1.C(NNC=O)=O>O>[C:13]1([C:11]2[N:10]=[N:9][NH:8][CH:12]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 123421,2-HydrazinedicarboxaldehydeHCID 1317347181-Phenyl-4-(tetradec-1-yl)triazolium bromide

Product 1

HCID 1784201274-phenyl-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

2.6 ml (2.64 g, 0.028 mol) aniline 1 and 2.5 g (0.028 mol) diformyl hydrazine are combined in a Schlenk flask. The flask is covered with a plastic lid loosely and the reaction mixture is stirred for 3 h at 180° C. Toward the end of the reaction time the lid is removed to allow produced reaction water to evaporate. After cooling down, 20 ml chloroform is added. The remaining diformyl hydrazine is filtered off and washed with chloroform. The combined chloroform phases are dried over sodium sulfate. 100 ml diethylether is added and the solution allowed to rest 3 days in the fridge for crystallizing. The precipitated precipitate is filtered off, washed with diethylether, and dried in vacuum.

Workup

  1. customToward the end of the reaction time the lid is removed
  2. customto allow produced
  3. customto evaporate
  4. temperatureAfter cooling down
  5. addition20 ml chloroform is added
  6. filtrationThe remaining diformyl hydrazine is filtered off
  7. washwashed with chloroform
  8. dry with materialThe combined chloroform phases are dried over sodium sulfate
  9. addition100 ml diethylether is added
  10. waitto rest 3 days in the fridge
  11. customfor crystallizing
  12. filtrationThe precipitated precipitate is filtered off
  13. washwashed with diethylether
  14. customdried in vacuum

Sources & evidence

ORD record
ord-f022860d248c42d8bbefa5694df01c8d
Source dataset
uspto-grants-2016_02
Patent number
US09260397B2

Reaction notes

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