Acetic Anhydride → N-(4-Phenoxyphenyl)acetamide

HRID 1466469Notes

Reaction equation

HRID 1466469 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.[C:22](OC(=O)C)(=[O:24])[CH3:23]>ClCCl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:12][C:22](=[O:24])[CH3:23])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8764(4-Aminophenoxy)benzene

Product 1

HCID 80579N-(4-Phenoxyphenyl)acetamideYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercial available 4-phenoxy-aniline (4.16 g, 20.8 mmol) was dissolved in dichloromethane (100 mL), and triethylamine (3.05 g, 31.1 mmol) and acetic anhydride (2.22 g, 20.8 mmol) were added in drops. The mixture was stirred for 1 h at 0° C. to room temperature. After completion of the reaction, the mixture was filtered using dichloromethane and crystallized to give the title compound (4.50 g, 18.6 mmol)

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered
  3. customcrystallized

Sources & evidence

ORD record
ord-137788353f0e4acfaa18cbfa46c1847f
Source dataset
uspto-grants-2015_04
Patent number
US09000028B2

Reaction notes

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