Water → 2-(Chloromethyl)-α-oxobenzeneacetamide

HRID 1636999Notes

Reaction equation

HRID 1636999 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].O.Cl.[O:15]1CCOCC1>C(OCC)(=O)C>[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:15]

Participants

5

Reactant 3

HCID 962Water2×HCID 9812919155380-13-5HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 109214932-(Chloromethyl)-α-oxobenzeneacetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Crude 2-(2-chloromethylphenyl)-2-oxoacetonitrile (purity: about 72%)(17.6 g), water (1.76 g) and 5N hydrogen chloride/dioxane solution (200 ml) were added into a round-bottom flask. The flask was stoppered, and then the mixture was stirred at room temperature for 3 days. After the reaction mixture was ice-cooled, water (150 ml) was added, and the mixture was stirred at room temperature for 40 minutes. The reaction mixture was diluted with ethyl acetate, and washed successively with a saturated aqueous solution of sodium bicarbonate, water and saturated brine. The ethyl acetate layer obtained was dried over anhydrous sodium sulfate and at the same time decolorized with Norit SX-3. Evaporation of the solvent under reduced pressure gave the crude product (16.6 g). The crude product was crystallized from ethyl acetate-hexane, and the crystallization mother liquor was purified by column chromatography on silica gel to obtain the title compound (11.3 g, total yield in the two steps: 57.3%, pale yellow crystals).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 40 minutes
  3. washwashed successively with a saturated aqueous solution of sodium bicarbonate, water and saturated brine
  4. customThe ethyl acetate layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate and at the same time
  6. customEvaporation of the solvent under reduced pressure
  7. customgave the crude product (16.6 g)
  8. customThe crude product was crystallized from ethyl acetate-hexane
  9. customthe crystallization mother liquor was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-37b8cfbfd1b841ddb25eb0fcdc985389
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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