Dichloromethane → O-Ethylacetanilide

HRID 2203211Notes

Reaction equation

HRID 2203211 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9])[CH3:6].CCN(CC)CC.C(Cl)Cl>O>[CH2:5]([C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH:9][C:1](=[O:3])[CH3:2])[CH3:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 113572-Ethylaniline

Product 1

HCID 36332O-EthylacetanilideYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetyl chloride was slowly added to a chilled mixture of 2-ethylaniline (12.1 g, 100 mmol), Et3N (20 mL, 145 mmol) and DCM (200 mL). Water (200 mL) was added and the layers separated. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated to give the title compound as a yellow solid (16 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.75 (1H, d, J=8.0 Hz), 7.20-7.24 (2H, m), 7.47 (1H, d, J=7.2 Hz), 6.95 (1H, s), 2.61 (2H, q, J=7.2 Hz), 2.21 (3H, s), 1.24 (3H, t, J=7.2 Hz).

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3e2b02b89e8545e39df6add549ce7793
Source dataset
uspto-grants-2016_06
Patent number
US09365566B2

Reaction notes

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