Triethylamine → ethyl 2-(4-methoxybenzyl)-2H-tetrazole-5-carboxylate

HRID 2384102Notes

Reaction equation

HRID 2384102 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][N:9]=[N:8][N:7]=1)=[O:5])[CH3:2].[Na].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[N:8][N:9]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[N:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1650214-Methoxybenzyl bromideHCID 178470519HCID 178470519, compound

Product 1

HCID 13596243ethyl 2-(4-methoxybenzyl)-2H-tetrazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium tetrazole-5-carboxylic acid ethyl ester (2 g, 12.19 mmol) in DMF (8 mL) is added 4-methoxybenzyl bromide (3.68 g, 18.28 mmol) followed by the addition of triethylamine (5.10 mL). The resulting mixture is stirred at room temperature overnight then ice/water is added. The mixture is extracted with EtOAc and the combined organic phases were washed with water and brine, dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography to afford 2-(4-methoxy-benzyl)-2H-tetrazole-5-carboxylic acid ethyl ester; HPLC Retention time 1.37 minutes (condition C): MS 263.2 (M+1).

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. washthe combined organic phases were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-e44e46246cbf4ff7b1235be920a796d5
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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