Hydrochloric Acid → HCID 178515925, compound

HRID 1839913Notes

Reaction equation

HRID 1839913 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[N-:10]=[N+:11]=[N-:12].[Na+].Cl>C1(C)C=CC=CC=1>[NH:10]1[C:1]([C:3]2[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=2)=[N:2][N:12]=[N:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 130194-CyanophenolHCID 33557Sodium Azide

Product 1

HCID 178515925HCID 178515925, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A 50 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar, and a rubber septum was charged with 4-cyanophenol (596 mg, 5.0 mmol), sodium azide (975 mg, 15 mmol), triethylamineo.HCl (2.06 g, 15 mmol) and toluene (25 mL). The reaction mixture was heated at 100° C. for 18 h with vigorous stirring. The reaction mixture was cooled to ambient temperature and poured into a separatory funnel and extracted with H2O (3×10 mL). The combined aqueous phases were treated dropwise with HCl (conc.) to precipitate the product from the reaction mixture. The precipitate was collected by vacuum filtration and dried under vacuum to afford the title compound as an off-white solid (890 mg, 94%).

Workup

  1. customA 50 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. additionpoured into a separatory funnel
  4. extractionextracted with H2O (3×10 mL)
  5. additionThe combined aqueous phases were treated dropwise with HCl (conc.)
  6. customto precipitate the product from the reaction mixture
  7. filtrationThe precipitate was collected by vacuum filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9f8762ba794f4d6aad04edabfd255a78
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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