Water → 1-(4-Nitrobenzyl)-1H-1,2,4-triazole

HRID 865698Notes

Reaction equation

HRID 865698 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na].[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(OCC)(=O)C.O>CN(C=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 660114-Nitrobenzyl bromideHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 64820001-(4-Nitrobenzyl)-1H-1,2,4-triazoleYield 51,913.602%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitrobenzylbromide (21.6 g, 0.1 mol) was added to a rapidly stirred suspension of 1,2,4-triazole sodium salt (9.1 g, 0.1 mmol) in anhydrous DMF (100 ml) and the mixture stirred at room temperature for 16 h. Ethyl acetate (400 ml) was added followed by water (250 ml) and the layers separated. The organic phase was washed with water (3×250 ml), dried (MgSO4) and evaporated. The residue was chromategraphed on silica gel eluting with ethyl acetate to give the title-product (10.6 g, 52%); m.p. 98°-100° C. δ (360 MHz, CDCl3) 5.47 (2H,s,CH2), 7.40 (2H, d, J=9 Hz, Ar--H), 8.02 (1H,s,Ar--H), 8.18 (1H, s, Ar--H), 8.23 (2H, d, J=9 Hz, Ar--H).

Workup

  1. customthe layers separated
  2. washThe organic phase was washed with water (3×250 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b495e50fd32546d3abe4c1c63f1f4cf1
Source dataset
uspto-grants-1996_10
Patent number
US05567726

Reaction notes

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