Hydrochloric Acid → 31656-78-7

HRID 614510Notes

Reaction equation

HRID 614510 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[N:2].Cl.N([O-])=O.[Na+].[N-:15]=[N+:16]=[N-].[Na+]>CCOCC.O.CCCCCC>[C:1]([C:3]1[CH:4]=[C:5]([N:6]=[N+:15]=[N-:16])[CH:7]=[CH:8][CH:9]=1)#[N:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 167023-AminobenzonitrileHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

Product 1

HCID 1180488331656-78-7

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A suspension of 9.44g. (0.08 mole) of 3-cyanoaniline in 50 ml. of water at 0° C. was treated with 20 ml. of concentrated HCl, with slow addition, maintaining the reaction mixture temperature at or below 5° C. There was then added a solution of 6.07g. (0.088 mole) of NaNO2 in 20 ml. of water, and the reaction mixture was aged for 1/2 hour at 0°-5° C. Then to the clear reaction mixture solution was added 75 ml. of hexane, followed by a solution of 5.72g. (0.088 mole) of NaN3 in 20 ml. of water, which were added dropwise with stirring. A precipitate was observed to form, after which 100 ml. of ether was added. The organic and aqueous components of the reaction mixture was separated and the aqueous component was extracted with 100 ml. of ether. The organic component was dried over MgSO4 and concentrated to a volume of about 100 ml. An aliquot was blown down and the structure of the product confirmed for 3-cyanophenylazide.

Workup

  1. additionA suspension of 9.44g
  2. temperaturemaintaining the reaction mixture temperature at or below 5° C
  3. additionThere was then added a solution of 6.07g
  4. additionThen to the clear reaction mixture solution was added 75 ml
  5. customto form
  6. customThe organic and aqueous components of the reaction mixture was separated
  7. extractionthe aqueous component was extracted with 100 ml
  8. dry with materialThe organic component was dried over MgSO4
  9. concentrationconcentrated to a volume of about 100 ml

Sources & evidence

ORD record
ord-e358ea023fdf402398535f9012f894dd
Source dataset
uspto-grants-1979_03
Patent number
US04145364

Reaction notes

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