Acetic Acid → HCID 178456866, compound

HRID 413948Notes

Reaction equation

HRID 413948 reaction equation
[CH2:1]([NH:4][C:5]1[NH:9][N:8]=[C:7]([NH2:10])[N:6]=1)[CH2:2][CH3:3].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)C1C=CC=CC=1.C(O)(=O)C>O>[CH:17](=[N:10][C:7]1[N:6]=[C:5]([NH:4][CH2:1][CH2:2][CH3:3])[NH:9][N:8]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 1140TolueneHCID 178456877HCID 178456877, compound

Product 1

HCID 178456866HCID 178456866, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5-liter flask equipped with a reflux condenser, thermometer, and mechanical stirrer was charged with 251.8 g (1.75 mole) of N5-Propyl-1H-[1,2,4]triazole-3,5-diamine, 1.75 liter of toluene, 203.4 g (1.92 mole) of benzaldehyde and 5.2 g (0.087 mole) of acetic acid and then heated to reflux for 1˜3 hours. During the reaction, water was formed as by-product and removed azeotropically. After checking the end of the reaction by LC (peak area of N5-Propyl-1H-[1,2,4]triazole-3,5-diamine is less than 1%), the mixture was cooled down and gave the crude N3-Benzylidene-N5-propyl-1H-[1,2,4]triazole-3,5-diamine suspension solution, which was used for the next stage without purification.

Workup

  1. customA 5-liter flask equipped with a reflux condenser
  2. temperatureheated
  3. temperatureto reflux for 1˜3 hours
  4. customDuring the reaction
  5. customremoved azeotropically
  6. customthe end of the reaction by LC (peak area of N5-Propyl-1H-[1,2,4]triazole-3,5-diamine is less than 1%)
  7. temperaturethe mixture was cooled down

Sources & evidence

ORD record
ord-15c0732fcaae4f5a954d3b146170be3e
Source dataset
uspto-grants-2003_05
Patent number
US06570014B1

Reaction notes

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