Hydrochloric Acid → HCID 178419015, compound

HRID 2268696Notes

Reaction equation

HRID 2268696 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-bottom 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 were heated at 120° C. for 8 hours. After cooling to room temperature, 100 ml of water were added and the mixture was admixed in an ice bath with dilute hydrochloric acid until no further precipitate was formed. The mixture was filtered with suction, the precipitate was washed with water and dried. Recrystallization from ethanol/water gave 4.4 g of colorless crystals.

Workup

  1. customIn a 250 ml round-bottom flask fitted
  2. temperaturewith reflux condenser
  3. customwas formed
  4. filtrationThe mixture was filtered with suction
  5. washthe precipitate was washed with water
  6. customdried
  7. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-ed80dd8e96de4c79892162a55cd45b4a
Source dataset
uspto-grants-2001_12
Patent number
US06329082B1

Reaction notes

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