Hydrochloric Acid → HCID 23323482, compound

HRID 1381129Notes

Reaction equation

HRID 1381129 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[F:12][C:13]1[CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.Cl>CN(C)C=O.O>[F:12][C:13]1[CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:17][C:18]=1[NH:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 98231-Fluoro-3-nitrobenzeneHCID 24758Sodium hydrideHCID 729132-Aminobenzonitrile

Product 1

HCID 23323482HCID 23323482, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

21.8 g (0.5 mol) of sodium hydride were added in portions to a solution of 59 g (0.5 mol) of 2-aminobenzonitrile and 53.2 ml (0.5 mol) of 3-fluoronitrobenzene in absolute dimethylformamide, whereby the reaction mixture warmed up to 80° C., with a change in colour from dark green to dark red. After the mixture had been cooled to room temperature, it was diluted with water and acidified with 2N hydrochloric acid, and the precipitate formed was filtered off. The precipitate was purified by chromatography over silica gel using dichloromethane, and the residue from evaporation of the product-containing fractions was thoroughly stirred with ether/petroleum ether 1:2.

Workup

  1. temperatureAfter the mixture had been cooled to room temperature
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. customThe precipitate was purified by chromatography over silica gel
  5. customthe residue from evaporation of the product-containing fractions

Sources & evidence

ORD record
ord-5eeb6bafb555451d9d3d65e3d60c6f9a
Source dataset
uspto-grants-1986_04
Patent number
US04585772

Reaction notes

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