Hydrochloric Acid → 4-Azidobenzoic acid

HRID 358227

Reaction equation

HRID 358227 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl.N([O-])=O.[Na+].[N-:16]=[N+:17]=[N-].[Na+]>O>[N:1]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 30341844-Azidobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

13.7 g of p-aminobenzoic acid was dispersed in a solution of 100 cc of water and 30 cc of 30% hydrochloric acid in an ordinary manner and the dispersion was cooled with ice. A solution of 8.3 g of sodium nitrite in 50 cc of water was added dropwise to the dispersion to effect the diazotization reaction. A solution of 10.1 g of sodium azide in 70 cc of water was added dropwise to the mixture, stirred for about one hour, filtered and vacuum-dried to obtain p-azidobenzoic acid. 5.4 g of the thus obtained p-azidobenzoic acid was dissolved in 10 cc of dimethylformamide and 25 g of thionyl chloride was added dropwise to the solution. The mixture was stirred for about one hour and the product was added dropwise to ice-water. After filtration followed by washing with water and vacuum drying, p-azidobenzoyl chloride was obtained.

Workup

  1. temperaturethe dispersion was cooled with ice
  2. customthe diazotization reaction
  3. filtrationfiltered
  4. customvacuum-dried

Sources & evidence

ORD record
ord-0b27ffc5dd0c4205b822984128c69f0e
Source dataset
uspto-grants-1984_08
Patent number
US04465768

Linked notes

Loading…