Hydrochloric Acid → 5-(4-Methylphenyl)-1H-tetrazole

HRID 2267966Notes

Reaction equation

HRID 2267966 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+].Cl>O.CN(C)C=O>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]2[N:2]=[N:10][NH:11][N:12]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7724p-TolunitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 2851645-(4-Methylphenyl)-1H-tetrazoleYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 117 grams (1.0 mole) of 4-cyanotoluene, 65.0 grams (1.0 mole) of sodium azide, and 12.0 grams (0.224 mole) of ammonium chloride 800 mL of N,N-dimethylformamide was heated at 130° C. for three hours. After this time the reaction mixture was cooled and then poured into 800 mL of water and 400 mL of ice. The resulting mixture was acidified to pH 2 with 3N hydrochloric acid, and the resulting solid was collected by filtration. The solid was washed with hexane, triturated with 300 mL of methanol, and dried under reduced pressure to a constant weight, yielding 115 grams of 4-(4-methylphenyl)-1,2,3,5-(1H)-tetrazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureAfter this time the reaction mixture was cooled
  2. filtrationthe resulting solid was collected by filtration
  3. washThe solid was washed with hexane
  4. customtriturated with 300 mL of methanol
  5. customdried under reduced pressure to a constant weight

Sources & evidence

ORD record
ord-9a1441a4b5f64430a5f8430b3bae6d68
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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