Hydrochloric Acid → HCID 178418369, compound

HRID 1034454Notes

Reaction equation

HRID 1034454 reaction equation
CN(C)C=O.[C:6](#[N:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:14]=[N+:15]=[N-:16].[Na+].Cl>[Cl-].[Zn+2].[Cl-].O>[C:7]1([C:6]2[NH:16][N:15]=[N:14][N:13]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7505BenzonitrileHCID 33557Sodium Azide

Product 1

HCID 178418369HCID 178418369, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 962WaterSolvent

Procedure

Zinc chloride (3.3g, 24.3 mmol, 0.5eq) was added to 15mL of N,N-dimethylformamide in small portions while maintaining the temperature below 60° C. The suspension of zinc chloride was cooled to room temperature and treated with 5.0 g of benzonitrile (48.5 mmol, 1.0 eq) followed by 3.2g of sodium azide (48.5 mmol, 1.0 eq). The heterogeneous mixture was heated at 115° C. with agitation for 18 hours. The mixture was cooled to room temperature, water (30 mL) was added and the mixture acidified by the addition of 5.1 mL of concentrated hydrochloric acid. The mixture was cooled to 0° C. and aged for one hour, then filtered and the filter cake washed with 15 mL of cold 0.1 N HCl then dried at 60° C. under vacuum to afford 6.38g (43.7 mmol, 90%) of the product.

Workup

  1. temperaturewhile maintaining the temperature below 60° C
  2. temperatureThe heterogeneous mixture was heated at 115° C. with agitation for 18 hours
  3. temperatureThe mixture was cooled to room temperature
  4. temperatureThe mixture was cooled to 0° C. and aged for one hour
  5. filtrationfiltered
  6. washthe filter cake washed with 15 mL of cold 0.1 N HCl
  7. customthen dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-ddc66ead809c4df1921193c5d2e2ebe0
Source dataset
uspto-grants-1994_05
Patent number
US05317017

Reaction notes

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