Hydrochloric Acid → HCID 54166889, compound

HRID 342169Notes

Reaction equation

HRID 342169 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:13])[C:10](N)=[O:11].Cl>C(O)CCCC>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:13])[C:10]([O:11][CH2:10][CH2:9][CH2:4][CH2:3][CH3:2])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 109214932-(Chloromethyl)-α-oxobenzeneacetamide

Product 1

HCID 54166889HCID 54166889, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

1.5 g (7.6 mmol) of 2-(chloromethyl)phenylglyoxylamide were initially introduced into 200 ml of n-pentanol. Hydrogen chloride was then introduced into the mixture as a gas until it was saturated, the temperature rising to 80° C. The mixture was then stirred for a further 3 hours and concentrated, the residue was treated with water and the mixture was extracted with methyl tert-butyl ether. The combined organic phases were washed with water, dried over sodium sulfate and concentrated. After purification by column chromatography on silica gel (methyl tert-butyl ether/n-hexane), 1.1 g (54% yield) of the title compound were obtained as a colorless oil.

Workup

  1. customrising to 80° C
  2. concentrationconcentrated
  3. additionthe residue was treated with water
  4. extractionthe mixture was extracted with methyl tert-butyl ether
  5. washThe combined organic phases were washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customAfter purification by column chromatography on silica gel (methyl tert-butyl ether/n-hexane)

Sources & evidence

ORD record
ord-4cd3faa94c564cc5aa9a61ba3b101b3d
Source dataset
uspto-grants-1999_01
Patent number
US05856560

Reaction notes

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