Aniline → Azidobenzene

HRID 1898614Notes

Reaction equation

HRID 1898614 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].[N-:12]=[N+:13]=[N-].[Na+]>O.Cl>[N:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N+:12]=[N-:13]

Participants

6

Reactant 3

HCID 6115AnilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 69319AzidobenzeneYield 91.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of aniline (300 mg, 3.22 mmol) in water (2 mL) and conc. HCl (1 mL) at 0° C. was slowly added a solution of sodium nitrite (289 mg, 4.19 mmol) in water (1 mL). The reaction mixture was stirred at 0° C. for 10 min then a solution of sodium azide (251 mg, 3.87 mmol) in water (1 mL) was slowly added. The reaction mixture was stirred at room temp for 1 h then extracted with Et2O (2×). The combined organics were washed with water, dried over MgSO4, and carefully concentrated at 300 torr and ambient temperature to afford 350 mg (91%) of azidobenzene as a light orange oil.

Workup

  1. stirringThe reaction mixture was stirred at room temp for 1 h
  2. extractionthen extracted with Et2O (2×)
  3. washThe combined organics were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationcarefully concentrated at 300 torr and ambient temperature

Sources & evidence

ORD record
ord-2c3c172f2852419b9911f4ca4ad29153
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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