Ethyl 3-aminobenzoate → ethyl 3-(1H-tetrazol-1-yl)benzoate

HRID 399794Notes

Reaction equation

HRID 399794 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(OC(OCC)OCC)C.[N-:23]=[N+:24]=[N-:25].[Na+].[C:27](=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[N:1]1([C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:27]=[N:25][N:24]=[N:23]1

Participants

7

Reactant 4

HCID 11400Ethyl 3-aminobenzoateHCID 11430Potassium CarbonateHCID 31214Ethyl orthoformateHCID 33557Sodium Azide

Product 1

HCID 18464674ethyl 3-(1H-tetrazol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The mixture of ethyl 3-aminobenzoate (3.0 g), tri(ethoxy)methane (3.0 ml) and sodium azide (1.2 g) in acetic acid (30 ml) was stirred for 5 hours at 60°-70° C. To the reaction mixture was added water and the mixture was adjusted to pH 8 with potassium carbonate. The isolated precipitate was collected by filtration and the precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran. The mixture was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethanol and diisopropyl ether to give ethyl 3-(1H-tetrazol-1-yl)benzoate (2.44 g).

Workup

  1. filtrationThe isolated precipitate was collected by filtration
  2. dissolutionthe precipitate was dissolved in a mixture of ethyl acetate and tetrahydrofuran
  3. washThe mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from a mixture of ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-978e852d57da4bd7ac1bb81c54f0e117
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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