Dimethylformamide → HCID 69205585, compound

HRID 30670Notes

Reaction equation

HRID 30670 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C:9]2[NH:13][N:12]=[N:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C)C=O.[H-].[Na+].I[CH2:24][CH3:25]>O>[CH2:24]([N:11]1[N:12]=[N:13][C:9]([CH2:8][C:7]2[CH:14]=[CH:15][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[N:10]1)[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178526616HCID 178526616, compound

Product 1

HCID 69205585HCID 69205585, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 5-(4-nitrobenzyl)-1H-tetrazole (5.0 g) and N,N-dimethylformamide (200 mL) was added sodium hydride (60% in oil, 1.17 g) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. and iodoethane (5.69 g) was added at 0° C. The reaction mixture was stirred at 0° C. for 2 hrs. and water was poured into the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 2-ethyl-5-(4-nitrobenzyl)-2H-tetrazole as a brown oil (2.70 g, yield 48%) from a fraction eluted with hexane-ethyl acetate (2:1-1:2, v/v).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 2 hrs
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5bb1d870530f408ab52d3b6f207a139d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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