Acetyl chloride → 2-Phenoxyacetanilide

HRID 1750914Notes

Reaction equation

HRID 1750914 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl>[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][C:22](=[O:24])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 75899Benzenamine, 2-phenoxy-

Product 1

HCID 8970802-PhenoxyacetanilideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The mixture of 2-phenoxyaniline (100 g, 540 mmol), triethylamine (0.090 L, 648 mmol) and 1 L dichloromethane was cooled to 0° C. by ice bath. Acetyl chloride (0.04 L, 567 mmol) was added dropwise. After the addition completed, the reaction was stirred under room temperature for 2 h. The mixture was concentrated and diluted by dichloromethane. The organic phase was washed by water and dried over sodium sulfate. The crude product was purified by silica gel column (20% EtOAc in hexane) to give red brown oily solid N-(2-phenoxyphenyl)acetamide (120 g, 98% yield).

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated
  3. additiondiluted by dichloromethane
  4. washThe organic phase was washed by water
  5. dry with materialdried over sodium sulfate
  6. customThe crude product was purified by silica gel column (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-1404d205651c425bac288e7484b73921
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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