Sodium Azide → HCID 178419288, compound

HRID 1472783Notes

Reaction equation

HRID 1472783 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Na+]>[Br-].[Zn+2].[Br-]>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:13][N:12]=[N:11][N:6]=2)[CH:7]=[C:8]([Br:10])[CH:9]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 27976903,5-Dibromobenzonitrile

Product 1

HCID 178419288HCID 178419288, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Conditions

Temperature
120 °C

Procedure

A round-bottomed flask was charged with 3,5-dibromobenzonitrile (15.65 g, 60.00 mmol), sodium azide (7.80 g, 120.00 mmol) and zinc bromide (27.00 g, 120.00 mmol). After degassed, DMF (100 mL) was added. The reaction mixture was heated to 120° C. and stirred at this temperature until complete. The reaction was cooled to rt and then in an ice-water bath. 300 mL of 1N aqueous HCl was added. The white precipitate formed was collected by suction filtration, washed with water, and dried together with phosphorous pentoxide under vacuum to afford 17.32 g (95%) of product.

Workup

  1. customAfter degassed
  2. additionDMF (100 mL) was added
  3. temperatureThe reaction was cooled to rt
  4. addition300 mL of 1N aqueous HCl was added
  5. customThe white precipitate formed
  6. filtrationwas collected by suction filtration
  7. washwashed with water
  8. dry with materialdried together with phosphorous pentoxide under vacuum

Sources & evidence

ORD record
ord-5cd89a6b16af4a81a98f3edf1b77d233
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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