Hydrochloric Acid → 5-(3-nitrophenyl)tetrazole

HRID 963507Notes

Reaction equation

HRID 963507 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8])([O-:3])=[O:2].[N-:12]=[N+:13]=[N-:14].[Na+].Cl.C(N(CC)CC)C.Cl>CN1CCCC1=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[NH:14][N:13]=[N:12][N:8]=2)[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 120793-NitrobenzonitrileHCID 33557Sodium Azide

Product 1

HCID 2851295-(3-nitrophenyl)tetrazoleYield 93.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-nitrobenzonitrile (3.70 g, 25 mmol), sodium azide (4.88 g, 75 mmol) and triethylamine hydrochloride (10.32 g, 75 mniol) in N-methylpyrrolidone (55 ml) was heated at 130° C. for 2 hours under stirring. The reaction mixture was poured into ice-water, to which was dropwise added 6N hydrochloric acid in order to acidify. The resultant precipitates were collected by filtration, washed with water and dried to afford 5-(3-nitrophenyl)-1H-tetrazole (4.45 g, 93.1%), which was used in a following reaction without further purification.

Workup

  1. customThe resultant precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b4977d2e8dce40dd8945e276bc302e29
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

Loading…