Ammonia → HCID 19003634, compound

HRID 1111162Notes

Reaction equation

HRID 1111162 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.CN(C)C([N:15]1[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]1)=O.[I-].[Na+].N>C(#N)C>[CH3:20][C:18]1[NH:17][C:16]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=2)=[N:15][CH:19]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 5238Sodium IodideHCID 869964-(Bromomethyl)benzonitrileHCID 14231157HCID 14231157, compound

Product 1

HCID 19003634HCID 19003634, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution containing alpha-bromo-4-tolunitrile (11.0 g), 1-(dimethylcarbamoyl)-4-methylimidazole (8.6 g) and sodium iodide (8.4 g) in acetonitrile (75 mL) is heated and stirred at reflux for 15 hours. The mixture is cooled to 0° (ice-bath) and ammonia gas is bubbled through the solution for 15 minutes. The volatiles are then evaporated and the residue is partitioned between water (150 mL) and ethyl acetate (150 mL). The organic solution is washed with water (2×50 mL) and is then extracted with 3N hydrochloric acid. The combined acidic extracts are made basic (pH 9) with 6N sodium hydroxide and the product is extracted into ethyl acetate (3×60 mL). After drying (MgSO4), solvent evaporation affords crude 4-[1-(5-methylimidazolyl)methyl]-benzonitrile which forms a hydrochloride salt, m.p. 203°-205°, when its solution in acetone is treated with ethereal HCl.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 15 hours
  3. customis bubbled through the solution for 15 minutes
  4. customThe volatiles are then evaporated
  5. customthe residue is partitioned between water (150 mL) and ethyl acetate (150 mL)
  6. washThe organic solution is washed with water (2×50 mL)
  7. extractionis then extracted with 3N hydrochloric acid
  8. extractionthe product is extracted into ethyl acetate (3×60 mL)
  9. customAfter drying
  10. custom(MgSO4), solvent evaporation

Sources & evidence

ORD record
ord-08135ae6628d4ddd835364719f9acd40
Source dataset
uspto-grants-1990_12
Patent number
US04978672

Reaction notes

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