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

HRID 1450471Notes

Reaction equation

HRID 1450471 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-0e0d1fd0a8b74ca186c75f64de55d3a0
Source dataset
uspto-grants-1997_02
Patent number
US05602162

Reaction notes

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