Pyridine → 1-benzyl-1H-tetrazole-5-carbonyl chloride

HRID 325727Notes

Reaction equation

HRID 325727 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([O-:15])=O)=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].N1C=CC=CC=1.C(Cl)(=O)C([Cl:26])=O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[C:12]([C:13]([Cl:26])=[O:15])=[N:11][N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 23688251Potassium 1-Benzyl-1H-tetrazole-5-carboxylate

Product 1

HCID 204638761-benzyl-1H-tetrazole-5-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of potassium 1-benzyl-1H-tetrazole-5-carboxylate (3.6 g; prepared as described in the specification of Belgian Pat. No. 845612), dry pyridine (0.75 ml) and dry toluene (65 ml) was cooled to 5° C. and treated with oxalyl chloride (12.5 ml). Stirring was maintained and the temperature was allowed to rise to 15° C. during a period of 2 hours. The mixture was filtered and the residue was washed with dry toluene. Evaporation of the combined toluene filtrate and washings, under diminished pressure, gave crude 1-benzyl-1H-tetrazole-5-carbonyl chloride in the form of an oil, which was used without further purification.

Workup

  1. customprepared
  2. temperaturewas maintained
  3. filtrationThe mixture was filtered
  4. washthe residue was washed with dry toluene
  5. customEvaporation of the combined toluene filtrate and washings

Sources & evidence

ORD record
ord-f1bee3e5b52a45299e62e87f2db85a7d
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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