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

HRID 42543

Reaction equation

HRID 42543 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.C(OCC)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

7

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 2

HCID 3283Diethyl EtherSolventHCID 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 reaction mixture was stirred for 4 hours. After this time, the reaction mixture was analyzed by LC/MS, which indicated that the reaction was not complete. As a result, the reaction was treated with benzyl chloromethyl ether (0.5 g, 3.19 mmol) and stirred for about 16 additional hours. At the conclusion of this period, the mixture was filtered, and the filtrate was concentrated in vacuo to yield a residue. The residue was diluted with diethyl ether (200 mL), washed 5× with water (50 mL), once with brine, dried over sodium sulfate, and then concentrated in vacuo. The resulting residue was purified over a 6×20 mm silica gel column, eluting with 20% then 30% ethyl acetate/hexanes to yield 2-(benzyloxymethyl)-2H-tetrazole (2.39 g, 44% yield) and 1-(benzyloxymethyl)-2H-tetrazole (2.56 g, 47% yield).

Workup

  1. stirringstirred for about 16 additional hours
  2. filtrationAt the conclusion of this period, the mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto yield a residue
  5. washwashed 5× with water (50 mL)
  6. dry with materialonce with brine, dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified over a 6×20 mm silica gel column
  9. washeluting with 20%

Sources & evidence

ORD record
ord-dbce395804984eb8bb043e9523eb5a17
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Linked notes

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