Water → N-(4-Phenoxyphenyl)acetamide

HRID 538616Notes

Reaction equation

HRID 538616 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-73c9c01ea6534c1cb00ea66838edfabf
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

Loading…