Hydrochloric Acid → 5-(3-nitrophenyl)tetrazole

HRID 2260795Notes

Reaction equation

HRID 2260795 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 85.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 3-cyanonitrobenzene (20 g) in 1-methyl-2-pyrrolidinone (200 ml) was added triethylamine hydrochloride (27.9 g) followed by sodium azide (26.4 g). The mixture was heated at 160° C. for 1.5 hours, then cooled to ambient temperature, poured into ice water (1000 ml) and acidified using 5M hydrochloric acid. 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) as a beige powder. mp 154°-156° C. 1H NMR (360 MHz, CDCl3) δ 7.59 (1H, dd, 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-f6a2114a34584d1f89d303853f5c78d1
Source dataset
uspto-grants-1995_12
Patent number
US05478933

Reaction notes

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