Acetanilide → N-acetyl-N-octylaniline

HRID 1022365Notes

Reaction equation

HRID 1022365 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:12])[CH3:11].[OH-].[K+].O>CS(C)=O>[C:10]([N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 904AcetanilideHCID 962WaterHCID 81401-Bromooctane2×HCID 14797Potassium Hydroxide

Product 1

HCID 66942989N-acetyl-N-octylanilineYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
52.5 °C

Procedure

1-Octylbromide (39 mL, 224 mmol, 1.12 eq) was added dropwise to a mixture of acetanilide (27 g, 200 mmol, 1 eq) in dimethylsulfoxide (130 mL), containing potassium hydroxide pellets (18.87 g, 300 mmol, 1.5 eq), at room temperature. After all the octyl bromide was added the reaction mixture was heated to 50-55° C. for 1.5 hours. The reaction mixture was cooled and poured into water (1 L), stirred for 45 minutes and extracted with hexanes (3×400 mL). The hexane extracts were combined, dried over sodium sulfate and evaporated to give 48.4 g (196 mmol, 98%) of colorless oil. The product was identified by NMR spectroscopy and mass spectrometry and was used without further purification.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with hexanes (3×400 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-3f28d0e615704d85aa0fc4e99f80f6b4
Source dataset
uspto-grants-2014_05
Patent number
US08722574B2

Reaction notes

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