Potassium Carbonate → 1-(benzyloxymethyl)-2H-tetrazole

HRID 1016179Notes

Reaction equation

HRID 1016179 reaction equation
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([O:14][CH2:13][N:2]1[N:3]=[N:4][CH:5]=[N:1]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:15]([O:14][CH2:13][N:1]1[CH:5]=[N:4][NH:3][NH:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl ether2×HCID 178418441HCID 178418441, compound

Product 2

HCID 107263402-((benzyloxy)methyl)-2H-tetrazoleYield 44%HCID 672998451-(benzyloxymethyl)-2H-tetrazoleYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-H-tetrazole (2.0 g, 28.5 mmol) and potassium carbonate (5.9 g, 42.7 mmol) in DMF (30 mL) was treated with benzyl chloromethyl ether (5.36 g, 34.2 mmol), and the mixture was stirred for 4 hours. Analysis by LC/MS indicated that the reaction was not complete, so the reaction was treated with benzyl chloromethyl ether (0.5 g, 3.19 mmol) and stirred overnight. The mixture was filtered, and the filtrate was concentrated in-vacuo. The residue was diluted with diethyl ether (200 mL), washed 5× with water (50 mL), once with brine, dried over sodium sulfate, and concentrated in-vacuo. The residue was purified over a 6×20 mm silica gel column, eluting with 20% then 30% ethyl acetate/hexanes to yield the title compound (2.39 g, 44% yield), and 1-(benzyloxymethyl)-2H-tetrazole (2.56 g, 47% yield).

Workup

  1. stirringstirred overnight
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in-vacuo
  4. additionThe residue was diluted with diethyl ether (200 mL)
  5. washwashed 5× with water (50 mL)
  6. dry with materialonce with brine, dried over sodium sulfate
  7. concentrationconcentrated in-vacuo
  8. customThe residue was purified over a 6×20 mm silica gel column
  9. washeluting with 20%

Sources & evidence

ORD record
ord-9e3632809eb14d998e770946a3548e0d
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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