Diethylaminoethyl chloride → HCID 21435349, compound

HRID 268375Notes

Reaction equation

HRID 268375 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 4 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 4 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8481c44bd58d4d49867f3e32305bc597
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

Loading…