Triethylamine hydrochloride → HCID 178519511, compound

HRID 1068923Notes

Reaction equation

HRID 1068923 reaction equation
Cl.C(N(CC)CC)C.[N-:9]=[N+:10]=[N-:11].[Na+].[C:13]([C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18])#[N:14]>CN1CCCC1=O>[NH:9]1[C:13]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH:17]=[O:18])=[N:14][N:11]=[N:10]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 1012092-Cyanobenzaldehyde

Product 1

HCID 178519511HCID 178519511, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

20.3 g (147 mmol) of triethylamine hydrochloride and 21.0 g (322 mmol) of sodium azide are added to a solution of 14.0 g (107 mmol) of 2-cyano-benzaldehyde in 350 ml of 1-methyl-2-pyrrolidone and heated at 110° C. for 3 hours (argon atmosphere). The black reaction solution is poured into 0.6 liter of ice/37% HCl (20:1) and stirred thoroughly to complete the reaction. Extraction with 3 portions of ethyl acetate, washing the organic phases with 3× water and brine, drying (Na2SO4), concentration by evaporation and stirring in diethyl ether yield 2-(tetrazol-5-yl)-benzaldehyde; m.p. 130° C.; TLC: Rf=0.10 (CHCl3/methano/H2O/acetic acid=85:13:1.5:0.5).

Workup

  1. customthe reaction
  2. extractionExtraction with 3 portions of ethyl acetate
  3. washwashing the organic phases with 3× water and brine
  4. customdrying
  5. concentration(Na2SO4), concentration
  6. customby evaporation
  7. stirringstirring in diethyl ether

Sources & evidence

ORD record
ord-60b81511f3b747479a096247da41a2c7
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

Loading…