Diethyl Ether → Acetamide, N-acetyl-N-phenyl-

HRID 861268Notes

Reaction equation

HRID 861268 reaction equation
C[NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5](NC)[CH:4]=1.C(O[C:15](=[O:17])[CH3:16])(=O)C.C([O:20][CH2:21][CH3:22])C>>[CH3:22][C:21]([N:2]([C:15]([CH3:16])=[O:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:20]

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 7918Acetic AnhydrideHCID 431636HCID 431636, compound

Product 1

HCID 137083Acetamide, N-acetyl-N-phenyl-

Procedure

To a solution of N,N'-dimethyl-1,3-benzenediamine (27.2 g, 0.20 mol) in ethyl ether (300 ml) is added acetic anhydride (44.8 g, 0.44 mol) over 20 minutes at room temperature. The mixture is stirred at room temperature for 2 hours. The solution is diluted with ether (300 ml) and washed with saturated sodium carbonate solution and water, dried over magnesium sulfate, and concentrated to a solid. The solid is recrystallized from ethyl acetate-hexane to give the pure diacetanilide.

Workup

  1. washwashed with saturated sodium carbonate solution and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to a solid
  4. customThe solid is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d63439c23d2e404f823855d5c6d89506
Source dataset
uspto-grants-1998_02
Patent number
US05714304

Reaction notes

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