Formamide → 1-(3-bromophenyl)-1H-1,2,4-triazole

HRID 586308Notes

Reaction equation

HRID 586308 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.Cl[CH2:12]Cl.[CH:14]([NH2:16])=O>>[Br:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:14]=[N:16][CH:12]=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 6344DichloromethaneHCID 337573-Bromophenylhydrazine hydrochloride

Product 1

HCID 223294981-(3-bromophenyl)-1H-1,2,4-triazole

Conditions

Temperature
140 °C

Procedure

A suspension of 3-bromophenylhydrazine hydrochloride (3.78 g, 17 mmol) in formamide (15 ml) was heated at 140° C. for 16 h. The reaction mixture was cooled to ambient temperature, diluted into dichloromethane (100 ml) and washed with water (2×100 ml). The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated to dryness to give 1-(3-bromophenyl)-1H-[1,2,4]triazole (3.44 g) as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.57 (1H, s), 8.11 (1H, s), 7.90 (1H, t, J 2 Hz), 7.62-7.64 (1H, m), 7.53-7.55 (1H, m), 7.38 (1H, t, J 8 Hz).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with water (2×100 ml)
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-a7865e92f6eb4314a71693e48f85655b
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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