Dimethylformamide → 1-(4-Bromo-2-ethyl-benzyl)-1H-[1,2,4]triazole

HRID 859675Notes

Reaction equation

HRID 859675 reaction equation
N1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[C:11](CC)[CH:10]=1.[CH3:19][N:20](C=O)[CH3:21]>CCOCC>[Br:8][C:9]1[CH:14]=[CH:13][C:5]([CH2:4][N:3]2[CH:21]=[N:20][CH:19]=[N:2]2)=[C:11]([CH2:12][CH3:15])[CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 587640754-Bromo-1-(bromomethyl)-2-ethylbenzeneHCID 178418936HCID 178418936, compound

Product 1

HCID 587640151-(4-Bromo-2-ethyl-benzyl)-1H-[1,2,4]triazoleYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

Triazole (275 mg, 3.99 mmol) dissolved in anhydrous DMF (15 mL) was treated with NaH (60%, 153 mg). After 5 min, 4-bromo-1-bromomethyl-2-ethyl-benzene was added. The reaction mixture was heated to 75° C. for 5 hours before it was cooled to room temperature. The mixture was diluted with Et2O and washed with H2O, brine, dried over MgSO4. The solvent was removed in vacuo to afford the desired product (580 mg, 55% yield). 1H NMR (300 MHz, CDCl3): δ 1.10 (t, J7.5 Hz, 3 H), 2.68–2.73 (m, 2 H), 5.46 (s, 2 H), 7.01–7.04 (m, 1 H), 7.38–7.46 (m, 2 H), 7.97–8.01 (m, 2 H).

Workup

  1. temperaturewas cooled to room temperature
  2. washwashed with H2O, brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f6f45dc125f34bafb04df89496038304
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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