Chloroacetyl chloride → 2-chloro-N-(4-phenoxyphenyl)acetamide

HRID 2108377Notes

Reaction equation

HRID 2108377 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[Cl:22][CH2:23][C:24]([NH:12][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[O:25]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 8764(4-Aminophenoxy)benzene

Product 1

HCID 7369692-chloro-N-(4-phenoxyphenyl)acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-phenoxyaniline (1.85 g, 10 mmoles) and triethylamine (2.07 ml, 15 mmoles) in 25 ml dry dichloromethane, is added stepwise a solution of chloroacetyl chloride (1.18 g, 10.5 mmoles) in 10 ml dry dichloromethane. The resulting reaction mixture is stirred for 1 hour at room temperature. Afterwards said reaction mixture is washed with 2×30 ml HCl (2 N) 1×30 ml water, dried with sodium sulfate and the solvent evaporated. 2.48 g. (Yield 95%) of 2-chloro-N-(4-phenoxyphenyl)acetamide were obtained.

Workup

  1. customThe resulting reaction mixture
  2. customAfterwards said reaction mixture
  3. washis washed with 2×30 ml HCl (2 N) 1×30 ml water
  4. dry with materialdried with sodium sulfate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-dc3a914405684e83aac56e64886c897b
Source dataset
uspto-grants-2009_04
Patent number
US07514429B2

Reaction notes

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