Hydrochloric Acid → 2-Azido-1,3-dichloro-benzene

HRID 424772Notes

Reaction equation

HRID 424772 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].Cl.N([O-])=O.[Na+].[N-:15]=[N+:16]=[N-].[Na+]>C(OCC)(=O)C.O>[N:4]([C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9])=[N+:15]=[N-:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 118462,6-DichloroanilineHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 116008082-Azido-1,3-dichloro-benzeneYield 90.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of 2,6-dichloroaniline (2.00 g) in ethyl acetate (40 mL) is added concentrated hydrochloric acid (12 mL). The reaction is stirred for 10 min. To this solution is added a solution of sodium nitrite (2.55 g) in water (7.5 mL) over 3 min. Upon completion of the addition, the reaction is stirred for an additional 30 min. A solution of sodium azide (2.41 g) in water (8 mL) is added over 5 min. After 30 min, pH 7 buffer (50 mL) is added and the reaction is transferred to a separatory funnel. The layers are separated and the aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (2.11 g). 1H NMR (400 MHz, CDCl3) δ 7.3-7.27 (d, 2H), 7.07-7.02 (t, 1H)

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction is stirred for an additional 30 min
  3. waitAfter 30 min
  4. additionpH 7 buffer (50 mL) is added
  5. customthe reaction is transferred to a separatory funnel
  6. customThe layers are separated
  7. extractionthe aqueous layer is extracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ef58be064314238b95b18c5f0ee47df
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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