HCID 178465660, compound → HCID 178433945, compound

HRID 1041756Notes

Reaction equation

HRID 1041756 reaction equation
[NH:1]=[C:2]([NH:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[CH3:3]>O>[CH3:3][C:2]1[NH:1][C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N+:13]([O-:15])=[O:14])=[N:5][N:4]=1

Participants

3

Reactant 1

HCID 178465660HCID 178465660, compound

Product 1

HCID 178433945HCID 178433945, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A suspension of 2-nitro-benzoic acid N′-(1-imino-ethyl)-hydrazide (4.3 g) in xylenes (50 mL) was refluxed in a flask fitted with a Dean-Stark trap. After 45 minutes of heating, the reaction suspension became a solution with a rapid condensation of water in the trap. The solution was cooled to −5° C. and stirred for 30 minute. The precipitated product was collected by filtration, washed with ice cold xylene twice, and dried in vacuo to provide 3.6 g of 3-methyl-5-(2-nitro-phenyl)-4H-[1,2,4]triazole: 1H NMR (300 MHz, CDCl3) δ 7.9-7.5 (m, 4H), 2.5 (s, 3H).

Workup

  1. temperaturewas refluxed in a flask
  2. customfitted with a Dean-Stark trap
  3. temperatureAfter 45 minutes of heating
  4. filtrationThe precipitated product was collected by filtration
  5. washwashed with ice cold xylene twice
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5b451055ce754430b1feae9a1c3f8459
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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