Chloroacetyl chloride → N-(4-chlorophenacyl) chloroacetamide

HRID 866850

Reaction equation

HRID 866850 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][NH2:9])=[CH:5][CH:4]=1.[OH-].[Na+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>C1C=CC=CC=1.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:7](=[O:10])[CH2:8][NH:9][C:17](=[O:18])[CH2:16][Cl:15])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 27982112-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

Product 1

HCID 53685377N-(4-chlorophenacyl) chloroacetamideYield 57.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

To a well stirred suspension of 20.6 g of 4-chlorophenacylamine hydrochloride in 70 ml of benzene and 70 ml of water which was cooled to below 7° C were added simultaneously 110 ml of 2N NaOH solution and 12.4 g of chloroacetyl chloride dissolved in 30 ml of benzene. After the addition was complete, the reaction mixture was warmed to room temperature and stirred at room temperature for 3 hours. At the end of this period, the formed precipitate was filtered, and the benzene layer was separated. The aqueous layer was extracted twice with 50 ml of benzene. The combined benzene layer was dried over anhydrous sodium sulfate, and evaporated to dryness. The residue together with the precipitate obtained above was combined and recrystallized from ethanol to give 14.1 g (57 percent) of N-(4-chlorophenacyl) chloroacetamide.

Workup

  1. temperaturewas cooled to below 7° C
  2. additionAfter the addition
  3. stirringstirred at room temperature for 3 hours
  4. filtrationAt the end of this period, the formed precipitate was filtered
  5. customthe benzene layer was separated
  6. extractionThe aqueous layer was extracted twice with 50 ml of benzene
  7. dry with materialThe combined benzene layer was dried over anhydrous sodium sulfate
  8. customevaporated to dryness
  9. customThe residue together with the precipitate obtained
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-83d612f9492a4e9883641d30e30df7d7
Source dataset
uspto-grants-1978_07
Patent number
US04101660

Linked notes

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