Dimethylformamide → 5-(3-nitrophenyl)tetrazole

HRID 1871453Notes

Reaction equation

HRID 1871453 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7](C#N)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl-].[NH4+].[N-:14]=[N+:15]=[N-:16].[Na+].[CH3:18][N:19](C=O)C>>[N+:1]([C:4]1[CH:5]=[C:6]([C:18]2[NH:19][N:16]=[N:15][N:14]=2)[CH:7]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 120904-NitrobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 2851295-(3-nitrophenyl)tetrazole

Conditions

Temperature
120 °C

Procedure

A mixture of 14.8 g of 4-nitrobenzonitril, 32 g of ammoniumchloride and 39 g of sodium azide in 150 ml of DMF was heated for 2 h at 120° C. After evaporating the solvent, the residue was partitioned between 2N hydrochloric acid and ethyl acetate. The organic layer was dried and evaporated. The residue was washed with ether and dried. M.p. 101-102° C.

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was partitioned between 2N hydrochloric acid and ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated
  5. washThe residue was washed with ether
  6. customdried

Sources & evidence

ORD record
ord-73ac118cbba84f05af0cdabac430908d
Source dataset
uspto-grants-2000_08
Patent number
US06103718

Reaction notes

Loading…