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

HRID 1637000Notes

Reaction equation

HRID 1637000 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:12])[C:10]#[N:11].Cl.[OH2:14]>>[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:12])[C:10]([NH2:11])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 9812919155380-13-5

Product 1

HCID 109214932-(Chloromethyl)-α-oxobenzeneacetamideYield 40.2%

Conditions

Temperature
40 °C

Procedure

A mixture of 2-(2-chloromethylphenyl)-2-oxoacetonitrile (1.80 g) and 36% hydrochloric acid aqueous solution (10 ml) was stirred at 40° C. for 20 hours. After the mixture was cooled by allowing it to stand, ice-cooled water was added, and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was extracted with ethyl acetate twice. The combined ethyl acetate layer was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave a crude product (0.89 g). The crude product was recrystallized from ethyl acetate-hexane to give the title compound (0.80 g, yield: 40.2%, pale yellow crystals).

Workup

  1. temperatureAfter the mixture was cooled
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. extractionThe mixture was extracted with ethyl acetate twice
  5. washThe combined ethyl acetate layer was washed successively with a saturated aqueous solution of sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent under reduced pressure
  8. customgave a crude product (0.89 g)
  9. customThe crude product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6baaa95b2ba64e7e8894bd9efffd9cef
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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