Diethylaminoethyl chloride → HCID 21435349, compound

HRID 2398475Notes

Reaction equation

HRID 2398475 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[O:8][C:9]3[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=3[C:11]=2[C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:29]([N:31]([CH2:35][CH3:36])[CH2:32][CH2:33]Cl)[CH3:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[O:8][C:9]3[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=3[C:11]=2[C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:30][CH2:29][N:31]([CH2:35][CH3:36])[CH2:32][CH3:33])=[CH:15][CH:14]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 24758Sodium hydrideHCID 21435284HCID 21435284, compound

Product 1

HCID 21435349HCID 21435349, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-(4-chlorobenzyl)-3-(4-hydroxybenzoyl)benzofuran (2.0 g., 5.5 mmol.) of 50 ml. of toluene is added to a slurry of 0.5 g. of a 57% sodium hydride dispersion (0.01 mol.) in 5 ml. of toluene. The reaction mixture is refluxed for 10 minutes, then 0.82 g. (5.5 mmol.) of 2-diethylaminoethyl chloride is added and the mixture is heated at 90° for four hours. The mixture is filtered and the filtrate concentrated under reduced pressure to give the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed for 10 minutes
  2. temperaturethe mixture is heated at 90° for four hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-247d86e7069c430c98df2cdf16ae3ca0
Source dataset
uspto-grants-1977_05
Patent number
US04024273

Reaction notes

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