Hydrazine, 1-naphthalenyl- → 3-(4-Bromo-phenyl)-1,5-di-naphthalen-1-yl-1H-[1,2,4]triazole

HRID 516496Notes

Reaction equation

HRID 516496 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:12][C:13]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)=O)OCC)=[CH:4][CH:3]=1.[C:25]1([NH:35][NH2:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:13]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[N:35]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[N:36]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 75240Hydrazine, 1-naphthalenyl-HCID 57610336Naphthalene-1-carboxylic acid 1-(4-bromo-phenyl)-1-ethoxy-methylideneamide

Product 1

HCID 576103533-(4-Bromo-phenyl)-1,5-di-naphthalen-1-yl-1H-[1,2,4]triazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
25 °C

Procedure

The compound obtained in step A) (1.0 g, 0.026 mol) and 1-naphthyl hydrazine (0.45 g, 0.028 mol) is dissolved in CCl4 (15 ml) and stirred for 10 hours at 25° C. under a nitrogen atmosphere. The reaction mixture is stirred for 12 hours and filtered to remove traces of insoluble particles. The CCl4 solution is then concentrated and a few drops of methanol are added to the residue, wherein a brownish solid is obtained (Yield=0.7 g (56%)).

Workup

  1. stirringThe reaction mixture is stirred for 12 hours
  2. filtrationfiltered
  3. customto remove traces of insoluble particles
  4. concentrationThe CCl4 solution is then concentrated
  5. additiona few drops of methanol are added to the residue, wherein a brownish solid
  6. customis obtained (Yield=0.7 g (56%))

Sources & evidence

ORD record
ord-d7c2db3732134b1683088925a9ff0fc8
Source dataset
uspto-grants-2015_08
Patent number
US09113536B2

Reaction notes

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