p-Tolunitrile → HCID 178424083, compound

HRID 532092Notes

Reaction equation

HRID 532092 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[N:8])=[CH:3][CH:2]=1.[N-:10]=[N+:11]=[N-:12].[Na+].Cl.C(NCC)C>C1(C)C=CC=CC=1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]2[NH:12][N:11]=[N:10][N:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7724p-TolunitrileHCID 33557Sodium AzideHCID 10197650Diethylammonium chloride

Product 1

HCID 178424083HCID 178424083, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In an environment of nitrogen, a mixture of p-tolunitrile (35.15 g, 300 mmol.), sodium azide (29.25 g, 450 mmol.), diethylamine hydrochloride (49.32 g, 450 mmol), and toluene (500 mL) was refluxed for 12 hours. After it was allowed to cool down, the beige suspension obtained was extracted with water (3×500 mL). Concentrated HCl was then drop-added into the water extracts to reach a pH value of around 3. The resulting white precipitates were filtered and dried in a vacuum oven all night. 5-(p-Tolyl)-1H-tetrazole in a form of white crystals (43.25 g, 90.0%) was obtained and used for the next step without any further purification.

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperatureto cool down
  3. customthe beige suspension obtained
  4. extractionwas extracted with water (3×500 mL)
  5. additionConcentrated HCl was then drop-added into the water
  6. customThe resulting white precipitates
  7. filtrationwere filtered
  8. customdried in a vacuum oven all night

Sources & evidence

ORD record
ord-8f8408d634094c338486cf2d213a8b35
Source dataset
uspto-grants-2014_10
Patent number
US08852755B2

Reaction notes

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