Triethylamine hydrochloride → methyl 3-(2H-1,2,3,4-tetrazol-5-yl)benzoate

HRID 349442Notes

Reaction equation

HRID 349442 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].[N-:12]=[N+:13]=[N-:14].[Na+].Cl.[CH2:17](N(CC)CC)C>C1(C)C=CC=CC=1.O>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([C:1]2[N:2]=[N:12][NH:13][N:14]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 158753-Cyanobenzoic acidHCID 33557Sodium Azide

Product 1

HCID 10536170methyl 3-(2H-1,2,3,4-tetrazol-5-yl)benzoateYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 3-cyanobenzoic acid (12.3 g, 0.083 mol) in toluene (300 mL) were added sodium azide (16 g, 0.25 mol) and triethylamine hydrochloride (34 g, 0.25 mol) respectively. The reaction mixture was refluxed for 4 hours, cooled to room temperature, and diluted with water (300 mL). The organic phase was separated and the aqueous portion was acidified (pH=1) using concentrated HCl. The precipitate was collected by filtration and oven-dried to give 14 g (89%) of the tetrazole as a white solid. CI-MS: C8H6N4O2 [M+1] 191.0. The product obtained (14 g, 0.074 mol) was suspended in anhydrous methanol followed by the addition of gaseous HCl over a period of 20 minutes. The warm solution was stirred at room temperature for overnight, then concentrated in vacuo. The resulting residue was triturated with diethyl ether and collected by filtration to yield 12.1 g (81%) of the methyl ester intermediate 2. CI-MS: C9H8N4O2 [M+1] 205.2

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customThe organic phase was separated
  3. filtrationThe precipitate was collected by filtration
  4. customoven-dried

Sources & evidence

ORD record
ord-8dcaf0ed857e4df3896144467be2d8c4
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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