Hydrochloric Acid → HCID 178419015, compound

HRID 356797

Reaction equation

HRID 356797 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[N-:15]=[N+:16]=[N-:17].[Na+].[Br-].C([NH+](CC)CC)C.Cl>CN(C=O)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]2[NH:17][N:16]=[N:15][N:10]=2)=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 12493Triethylamine hydrobromideHCID 33557Sodium AzideHCID 778834-tert-ButylbenzonitrileHCID 433294Lithium Chloride

Product 1

HCID 178419015HCID 178419015, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 250 ml round-bottomed flask fitted with reflux condenser, 4.9 g of p-t-butylbenzonitrile, 3.82 g of lithium chloride and 5.85 g of sodium azide and 8.2 g of triethylammonium bromide in 100 ml of DMF are heated at 120° C. for 8 hours. After cooling to room temperature, 100 ml of water are added and the mixture is admixed in an ice bath with dilute hydrochloric acid until no further solid precipitates. The precipitate is filtered off with suction, washed with water and dried. Recrystallization from ethanol/water gives 4.4 g of colorless crystals.

Workup

  1. customIn a 250 ml round-bottomed flask fitted
  2. temperaturewith reflux condenser
  3. customprecipitates
  4. filtrationThe precipitate is filtered off with suction
  5. washwashed with water
  6. customdried
  7. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-31833a1e0ad14612875a81cff3bd5702
Source dataset
uspto-grants-1998_11
Patent number
US05840217

Linked notes

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