Ethyl orthoformate → 4'-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid methyl ester

HRID 217322Notes

Reaction equation

HRID 217322 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4].[N-:19]=[N+:20]=[N-:21].[Na+].[CH:23](OCC)(OCC)OCC>CC(O)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([N:11]2[CH:23]=[N:21][N:20]=[N:19]2)[CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 578511214'-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid methyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (10 g, 41.5 mmol) and NaN3 (4.99 g, 76.76 mmol) in AcOH (80 mL) was added HC(OEt)3 (29.5 g, 199.2 mmol) at room temperature, then heated to reflux for 4 h. The solvent was removed in vacuo and the residue was purified by silica-gel chromatography to give 4′-Methyl-5-tetrazol-1-yl-biphenyl-3-carboxylic acid methyl ester as light yellow solid (11.22 g, 92%). MS (M+H)=295.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-99ab9c23f6144dc3ac40b02f3d5b24ce
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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