Hydrochloric Acid → HCID 13961197, compound

HRID 1197119Notes

Reaction equation

HRID 1197119 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]#N)=[CH:7][C:6]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])(=O)C.Cl.[OH2:24].[CH2:25]([OH:27])[CH3:26]>>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:27][CH2:25][CH3:26])=[O:24])=[CH:7][C:6]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 13961196HCID 13961196, compound

Product 1

HCID 13961197HCID 13961197, compound

Procedure

32.2 g (0.1 mol) of 4-acetamido-3-(2-chlorobenzoyl)-phenylacetonitrile are dissolved in 340 ml of absolute ethanol. While cooling in ice, dry gaseous hydrogen chloride is passed in for one hour. The mixture is subsequently refluxed for 30 minutes and then stirred at room temperature for 24 hours. Five times the amount of water is added to the reaction mixture, which is left to stand for 15 minutes. Extraction with dichloromethane, drying and concentration of the organic phase is followed by working out by chromatography on silica gel results in 20.9 g (64% of theory) of the title compound as an oil.

Workup

  1. temperatureWhile cooling in ice
  2. customis passed in for one hour
  3. temperatureThe mixture is subsequently refluxed for 30 minutes
  4. waitis left
  5. waitto stand for 15 minutes
  6. extractionExtraction with dichloromethane
  7. customdrying

Sources & evidence

ORD record
ord-84f8778436c14e72b6ce51c05d6d207c
Source dataset
uspto-grants-1992_05
Patent number
US05116971

Reaction notes

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