Water → 1-(4-Nitrophenyl)4-propyl-5-tetrazolone

HRID 1004633Notes

Reaction equation

HRID 1004633 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[N:13]=[N:12][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].Br[CH2:19][CH2:20][CH3:21].O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[N:13]([CH2:19][CH2:20][CH3:21])[N:12]=[N:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 14797Potassium HydroxideHCID 178518974HCID 178518974, compound

Product 1

HCID 151254851-(4-Nitrophenyl)4-propyl-5-tetrazoloneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 1-(4-nitrophenyl)-5-tetrazolone (6 g) in anhydrous N,N-dimethylformamide (30 mL) was added powdered 85% potassium hydroxide (1.9 g) and 1-bromopropane (3.9 g). The mixture was stirred at 55° C. for 2 hours and then poured into 300 mL of water. The biphasic mixture was extracted with ethyl acetate, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, ethyl acetate:hexane) to afford 7.2 g of the title compound as a pale yellow solid. 1H NMR (CDCl3) δ 8.32 (ABq, JAB =9.6 Hz, 4 H), 4.02 (t, J=7.2 Hz, 2 H), 1.93 (m, 2 H), 1.03 (t, J=7.5 Hz, 3 H); MS (CI) m/z 250 (MH+); Rf =0.6 (25% ethyl acetate/hexane).

Workup

  1. extractionThe biphasic mixture was extracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (silica gel, ethyl acetate:hexane)

Sources & evidence

ORD record
ord-d74811bfc4f14f9a9430b22f4a5b30c4
Source dataset
uspto-grants-2000_04
Patent number
US06051586

Reaction notes

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