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

HRID 2399705Notes

Reaction equation

HRID 2399705 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 52%

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 mol) 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 chromatographed 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
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-117a295223fb41489a7bac7b597ada1d
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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