Triethylamine hydrochloride → HCID 178497695, compound

HRID 591793Notes

Reaction equation

HRID 591793 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[N-:14]=[N+:15]=[N-:16].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[NH:16][N:15]=[N:14][N:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 848548Methyl 4-(cyanomethyl)benzoate

Product 1

HCID 178497695HCID 178497695, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-cyanomethyl benzoic acid methyl ester (2.63 g, 15 mmol) in anhydrous toluene (100 mL) was added sodium azide (1.95 g, 30 mmol) and triethylamine hydrochloride (4.13 g, 30 mmol). The reaction mixture was stirred at 100° C. for 24 hours under nitrogen. The reaction mixture was cooled to room temperature, then extracted with water (2×100 mL). The aqueous layer was acidified with concentrated HCl to pH approximately 4. The white solid was filtered off, washed with water, and dried under vacuum at 40° C. overnight, to give methyl-4-(1H-tetrazol-5-ylmethyl)benzoate (2.88 g, 88%) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with water (2×100 mL)
  3. filtrationThe white solid was filtered off
  4. washwashed with water
  5. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-b24d37d299b34543b77d2f6b5cc537e8
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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