Water → 3-(4-Bromo-3-methylphenyl)-4,5-dimethyl-1,2,4-triazole

HRID 1741064Notes

Reaction equation

HRID 1741064 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH3:13])[NH:10][N:9]=2)=[CH:4][C:3]=1[CH3:14].[H-].[Na+].I[CH3:18].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:18])[C:11]([CH3:13])=[N:10][N:9]=2)=[CH:4][C:3]=1[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 218338103-(4-Bromo-3-methylphenyl)-5-methyl-1,2,4-triazole

Product 1

HCID 218337813-(4-Bromo-3-methylphenyl)-4,5-dimethyl-1,2,4-triazoleYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Bromo-3-methylphenyl)-5-methyl-1,2,4-triazole (D62, 0.60 g, 2.4 mmol) was stirred under Ar in dry DMF (6 ml) as sodium hydride (80% dispersion, 0.21 g, 7.2 mmol) was added. After stirring for 30 min, iodomethane (0.3 ml, 4.8 mmol) was added. This mixture was stirred for 1 h, and treated with water (30 ml), giving a beige precipitate. This was filtered off and dried, giving the title compound (0.49 g, 77%) as a beige solid. 1H NMR (250 MHz, d6DMSO) δ(ppm): 7.92 (s, 1H), 7.65 (m, 2H), 3.80 (s, 3H), 2.44 (s, 3H), 2.39 (s, 3H).

Workup

  1. additionwas added
  2. stirringThis mixture was stirred for 1 h
  3. customgiving a beige precipitate
  4. filtrationThis was filtered off
  5. customdried

Sources & evidence

ORD record
ord-a8a4d5b81b784f3bae6b4736f793c8ec
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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