Chloroacetyl chloride → HCID 12855597, compound

HRID 544524Notes

Reaction equation

HRID 544524 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH3:11])=[C:6]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[Cl:22][CH2:23][C:24]([N:8]([CH2:9][CH2:10][CH3:11])[C:7]1[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=1[O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[O:25]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 20458093HCID 20458093, compound

Product 1

HCID 12855597HCID 12855597, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing a portion of the 6-methyl-2-[2-(2-methoxyethoxy)ethoxy]-N-2-methylethyl aniline (5.34 g; 0.02 mole) and sodium hydroxide (0.88 g; 0.22 mole) in 150 ml. of methylene chloride was cooled to 10° C. To the reaction mixture was added dropwise chloroacetyl chloride (2.5 g; 0.022 mole) and the resulting mixture was stirred for 10 minutes. The layers were separated and the organic methylene chloride layer was washed with water, dried over magnesium sulfate and concentrated in vacuo to yield a crude product. The crude product was separated on a silica gel column using a 2:5 ethyl acetate:cyclohexane mixture as the eluant to yield 2-chloro-N-2-methylethyl-N-[6-methyl-2-(2-(2-methoxyethoxy)ethoxy)phenyl]acetamide (Compound No. 102) (2.7 g; 39% yield) as a clear yellow oil having a boiling point of 163° C. (0.13 mmHg) and the following analysis:

Workup

  1. customThe layers were separated
  2. washthe organic methylene chloride layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield a crude product
  6. customThe crude product was separated on a silica gel column

Sources & evidence

ORD record
ord-5caf168b3b1943c88c8d380fb55b4734
Source dataset
uspto-grants-1984_05
Patent number
US04451285

Reaction notes

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