Hydrochloric Acid → 2-(Chloromethyl)-α-oxobenzeneacetamide

HRID 342168Notes

Reaction equation

HRID 342168 reaction equation
[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([C:7]#[N:8])=[O:6].Cl.[OH2:14]>>[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](=[O:6])[C:7]([NH2:8])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 9812919155380-13-5

Product 1

HCID 109214932-(Chloromethyl)-α-oxobenzeneacetamideYield 74%

Procedure

16.5 g (92 mmol) of 2-(chloromethyl)benzoyl cyanide, 150 ml of concentrated hydrochloric acid and 150 ml of saturated ethereal hydrogen chloride solution were mixed together and stirred at room temperature for 5 hours. The mixture was then poured into water, the organic phase was separated off and the aqueous phase 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), 13.4 g (74% yield) of the title compound were obtained as a beige powder of melting point 105°-107° C.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted with methyl tert-butyl ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customAfter purification by column chromatography on silica gel (methyl tert-butyl ether/n-hexane)

Sources & evidence

ORD record
ord-f0be74d52b6b4a1386bf2c927e1a45c1
Source dataset
uspto-grants-1999_01
Patent number
US05856560

Reaction notes

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