Triethylamine → 2,3-Dimethyl-7-[1,2-di(diethylamino)ethyl]benzofuran

HRID 1107514Notes

Reaction equation

HRID 1107514 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH:12]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:13]O)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[CH2:20]([N:22](CC)[CH2:23][CH3:24])[CH3:21].S(Cl)(C)(=O)=O>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH:12]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:13][N:22]([CH2:23][CH3:24])[CH2:20][CH3:21])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 154079562,3-Dimethyl-7-(1-diethylamino-2-hydroxyethyl)benzofuran

Product 1

HCID 187875122,3-Dimethyl-7-[1,2-di(diethylamino)ethyl]benzofuranYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

0.8 g (2.7 mmol) of 2,3-dimethyl-7-(1-diethylamino-2-hydroxyethyl)benzofuran, 2.67 ml (19.2 mmol) of triethylamine and 50 ml of dichloromethane are placed in a 100 ml round-bottomed flask. The solution is cooled to -30° C. using a dry ice bath and 99 ml (12.8 mmol) of mesyl chloride are added dropwise. The temperature is allowed to return to 0° C. and the solution is concentrated under vacuum. 20 ml of diethylamine are added to the residue and the solution obtained is heated at reflux for 16 hours. The reaction mixture is cooled to room temperature and concentrated under vacuum, 50 ml of water are added and extraction is carried out with ethyl acetate. The organic phases are combined, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a silica column (elution solvent: 10% methanol in dichloroethane). 0.434 g (Yield: 55%) of 2,3-dimethyl-7-[1,2-di(diethylamino)ethyl]benzofuran is obtained in the form of an oil.

Workup

  1. customto return to 0° C.
  2. concentrationthe solution is concentrated under vacuum
  3. addition20 ml of diethylamine are added to the residue
  4. customthe solution obtained
  5. temperatureis heated
  6. temperatureat reflux for 16 hours
  7. temperatureThe reaction mixture is cooled to room temperature
  8. concentrationconcentrated under vacuum, 50 ml of water
  9. additionare added
  10. extractionextraction
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated under vacuum
  13. customThe residue is purified by chromatography on a silica column (elution solvent: 10% methanol in dichloroethane)

Sources & evidence

ORD record
ord-8d7a2452e03947539a72c6a5dd2fd53d
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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