Hydrazine hydrate (1:1) → 3-(4-Bromo-2-fluoro-5-methylphenyl)-1H-1,2,4-triazole

HRID 717150Notes

Reaction equation

HRID 717150 reaction equation
[Br:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([C:6]([N:8]=[CH:9][N:10](C)C)=O)=[C:4]([F:16])[CH:3]=1.O.[NH2:18]N>C(O)(=O)C>[Br:1][C:2]1[C:14]([CH3:15])=[CH:13][C:5]([C:6]2[N:8]=[CH:9][NH:10][N:18]=2)=[C:4]([F:16])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 666078964-Bromo-N-[(dimethylamino)methylene]-2-fluoro-5-methylbenzamide

Product 1

HCID 1784234293-(4-Bromo-2-fluoro-5-methylphenyl)-1H-1,2,4-triazoleYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-bromo-N-((dimethylamino)methylene)-2-fluoro-5-methylbenzamide (24.6 g, 86.2 mmol) in acetic acid (200 mL) was added dropwise hydrazine hydrate (25 mL, 0.70 mol) at 0° C. The reaction mixture was stirred at room temperature overnight. The mixture was filtered washed with water (500 mL×3) and dried under reduced pressure to give the title compound (15 g, 68% yield) as a white solid. MS (ESI) m/z 256.0 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with water (500 mL×3)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-e1a32d7c8f64484d8dccf2426e4e72df
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

Loading…