Chloroacetyl chloride → HCID 20315556, compound

HRID 2419360Notes

Reaction equation

HRID 2419360 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([N:7]([CH2:18][CH3:19])[C:8](=[O:17])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:6].[Cl:20][CH2:21][C:22](Cl)=[O:23]>C(Cl)Cl>[CH2:18]([N:7]([CH2:5][CH3:6])[C:8](=[O:17])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:22](=[O:23])[CH2:21][Cl:20])=[CH:13][CH:12]=1)[CH3:19]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 19228Phenoxyacetic N,N-diethylamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20315556HCID 20315556, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (83.3g.) was added in portions over 30 minutes to a rapidly stirred solution of N,N-diethylphenoxyacetamide (51.6g.) and chloroacetyl chloride (31.0g.) in methylene dichloride (200ml.) at 0° C. The mixture was stirred and allowed to reach room temperature over 16 hours. The solvent was evaporated and the residue poured into a mixture of ice (300g.) and concentrated hydrochloric acid (15ml.). The mixture was extracted with methylene dichloride (5 × 100ml.), and the extracts washed with water (2 × 50ml.) dried and evaporated. The residue was chromatographed on alumina to give N,N-diethyl-4-(chloroacetyl)phenoxyacetamide, m.p. 89°-91° C.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue poured into a mixture of ice (300g.) and concentrated hydrochloric acid (15ml.)
  3. extractionThe mixture was extracted with methylene dichloride (5 × 100ml.)
  4. washthe extracts washed with water (2 × 50ml.)
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on alumina

Sources & evidence

ORD record
ord-307482f656da43fbbf944ae7dbb9da7b
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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