Hydrochloric Acid → 5-(3-nitrophenyl)tetrazole

HRID 2399679Notes

Reaction equation

HRID 2399679 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.C(N(CC)CC)C.[N-:20]=[N+:21]=[N-:22].[Na+].Cl>CN1CCCC1=O>[N+:9]([C:5]1[CH:4]=[C:3]([C:1]2[NH:22][N:21]=[N:20][N:2]=2)[CH:8]=[CH:7][CH:6]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

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

Product 1

HCID 2851295-(3-nitrophenyl)tetrazoleYield 88.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 3-cyanonitrobenzene (20 g, 0.13 mol) in 1-methyl-2-pyrrolidinone (200 mg) was added triethylamine hydrochloride (27.9 g, 0.20 mol) followed by sodium azide (26.4 g, 0.40 mol). The mixture was heated at 160° C. for 1.5 h, then cooled to ambient temperature, poured into ice water (100 mg) and acidified using 5M HCl. The solid which precipitated from the mixture was filtered, washed with water and dried under vacuum at 50° C. to afford the title tetrazole (22.1 g, 86%) as a beige powder, mp 154°-156° C. 1H NMR (360 MHz, CDCl13) δ 7.59 (1H, t, J=8 Hz), 8.19 (1H, d, J=8 Hz), 8.36 (1H, d, J=8 Hz), 8.86 (1H, s).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe solid which precipitated from the mixture
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-6fa74bfea86240a08324778092caad69
Source dataset
uspto-grants-1995_09
Patent number
US05451582

Reaction notes

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