Triethylamine hydrochloride → HCID 178519552, compound

HRID 1068919Notes

Reaction equation

HRID 1068919 reaction equation
Cl.C(N(CC)CC)C.[N-:9]=[N+:10]=[N-:11].[Na+].[C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])#[N:14]>CN1CCCC1=O>[NH:9]1[C:13]([C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=2)[CH:18]=[O:19])=[N:14][N:11]=[N:10]1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 90670m-Formylbenzonitrile

Product 1

HCID 178519552HCID 178519552, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

5.8 g (42.1 mmol) of triethylamine hydrochloride and 6.0 g (92.3 mmol) of sodium azide are added to a solution of 4.0 g (30.5 mmol) of 3cyano-benzaldehyde in 100 ml of 1-methyl-2-pyrrolidone and heated at 110° C. for 1.5 hours (argon atmosphere). When cool the reaction mixture 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 3-(tetrazol-5-yl)-benzaldehyde; m.p. 185-189° C.; TLC: Rf=0.13 (CHCl3/methanol/H2O/acetic acid=85:13:1.5:0.5).

Workup

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

Sources & evidence

ORD record
ord-379ea090e8da47ec9cc7ca745cc562ce
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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