Ethanol → HCID 14934996, compound

HRID 2382616Notes

Reaction equation

HRID 2382616 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])[CH3:2].[CH2:10](O)[CH3:11].C(=O)([O-])[O-].[Na+].[Na+].[CH2:19](I)[CH3:20]>O>[CH2:19]([N:6]([CH2:10][CH3:11])[C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([CH2:1][CH3:2])[CH:4]=1)[CH3:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 114753-Ethylaniline

Product 1

HCID 14934996HCID 14934996, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a 100 cm3 round bottom flask was added 3-ethylaniline (5.0 g, 41.3 mmol), ethanol (7.5 cm3), sodium carbonate (5.9 g, 55.7 mmol). Ethyl iodide (17.38 g, 111.4 mmol) was added dropwise. The mixture was then heated at 45° C. for 12 hours before cooling to room temperature and adding water (50 cm3). The mixture was extracted into diethyl ether (3×50 cm3) the extracts were dried over magnesium sulphate, filtered, and concentrated to give the title compound (7.03 g, 96%) as a light yellow oil. δH (250 MHz; CDCl3): 7.20 (1H, dd, 9, 7.25, ArH), 6.60 (3H, m, ArH), 3.43 (4H, q, 7, NCH2), 2.69 (2H, q, 7.25, CH2), 1.32 (3H, t, 7.5, CH3), 1.23 (6H, t, 7, CH3); δC (62.9 MHz; CDCl3): 12.7 (CH3), 15.8 (CH3), 29.5 (CH2), 44.4 (NCH3), 109.4 (ArC), 111.4 (ArC), 115.1 (ArC), 129.2 (ArC), 145.4 (ArC), 147.9 (ArC).

Workup

  1. temperaturebefore cooling to room temperature
  2. extractionThe mixture was extracted into diethyl ether (3×50 cm3) the extracts
  3. dry with materialwere dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8998606f7a8049778d525e3ea25073fc
Source dataset
uspto-grants-2012_09
Patent number
US08263589B2

Reaction notes

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