Dimethylformamide → HCID 178428098, compound

HRID 471456Notes

Reaction equation

HRID 471456 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5](C#N)=[CH:4][C:3]=1[CH3:11].[N-:12]=[N+:13]=[N-:14].[Na+].[Cl-].[NH4+].[CH3:18][N:19](C)C=O>O>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([N:13]2[N:14]=[CH:18][NH:19][NH:12]2)=[CH:8][C:9]=1[CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 110850704-Bromo-3,5-dimethyl-benzonitrile

Product 1

HCID 178428098HCID 178428098, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

4-Bromo-3,5-dimethyl benzonitrile (3.0 g, 14.3 mmol), sodium azide (2.32 g, 35.7 mmol) and ammonium chloride (2.3 g, 42.84 mmol) are suspended in dry N,N-dimethylformamide and heated at 140° C. for 7 hours. The mixture is allowed to cool to room temperature, diluted with water and the precipitated solid collected by filtration, washed with water and dried to give the title compound (yield 1.74 g). The mother liquor was saturated with sodium chloride and repeatedly extracted with ethyl acetate. The organic extracts were combined and the solvent removed to give a second crop of title compound (yield 1.39 g, total yield 3.13 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitated solid collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0895e80ecd6043b5802516dc1cf69599
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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