Water → N-(4-Phenoxyphenyl)acetamide

HRID 415690Notes

Reaction equation

HRID 415690 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[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].O>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:22](=[O:24])[CH3:23])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8764(4-Aminophenoxy)benzene

Product 1

HCID 80579N-(4-Phenoxyphenyl)acetamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To an ice-cold solution of 4-phenoxy-phenylamine (1.0 g, 5.39 mmol) in 10 ml of DCM was added triethylamine (0.90 ml, 5.93 mmol) followed by acetyl chloride (0.50 g, 6.47 mmol). The reaction mixture was stirred at 25° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), water was added extracted with DCM (3×50 mL). The combined organics was dried (Na2SO4), filtered and concentrated to get the desired product (1.20 g, crude yield).

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialThe combined organics was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1faef7174de54dba99cbe8e926f551a4
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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