Acetic Anhydride → N-(4-Ethylphenyl)acetamide

HRID 2182404Notes

Reaction equation

HRID 2182404 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].C(N(CC)CC)C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>ClCCl>[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:17](=[O:19])[CH3:18])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 115044-Ethylaniline

Product 1

HCID 72893N-(4-Ethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-ethylaniline (2 g) and triethylamine (13.91 mL) in dichloromethane (40 mL) at 0° C. under nitrogen was treated dropwise with acetic anhydride (4.67 mL). The mixture was warmed to ambient temperature, then stirred for 16 hours at room temperature, then washed with (i) 10% citric acid (40 mL), (ii) water (40 mL) and (iii) brine (40 mL). The organic phase was dried over magnesium sulfate and then evaporated to give 4-ethyl-N-acetyl-aniline (2.36 g) as a pale orange solid which was used without further purification. LC-MS (METHOD B): RT=2.80 minutes; 164.2 (M+H)+. (b) 3-Methyl-4-isopropyl-N-acetyl aniline

Workup

  1. washwashed with (i) 10% citric acid (40 mL), (ii) water (40 mL) and (iii) brine (40 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-88b74dc86c4f4a3f80447ff247fa6266
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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