Thionyl Chloride → HCID 19820420, compound

HRID 1030465Notes

Reaction equation

HRID 1030465 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18]O)=[C:8]([O:22][CH2:23][CH2:24][NH:25][CH3:26])[CH:7]=1>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][Cl:3])=[C:8]([CH:7]=1)[O:22][CH2:23][CH2:24][NH:25][CH3:26]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19820418HCID 19820418, compound

Product 1

HCID 19820420HCID 19820420, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 15 ml of thionylchloride in 200 ml of toluene was added at room temperature to a solution of 20.1 g of 2-[4-chloro-2-[2-(methylamino)ethoxy]phenoxy]benzeneethanol in 400 ml of dry toluene. After 30 min of stirring the mixture was concentrated, dissolved in water and washed with diethyl ether. The aqueous layer was basified with 2N sodium hydroxide and extracted with diethyl ether. The ethereal layer was dried over sodium sulphate, concentrated in vacuo and purified by silica chromatography using toluene-ethanol (8:2) to obtain 12.9 g (61%) of 2-[5-chloro-2-[(2-chloroethyl)phenoxy]phenoxy]-N-methyl-ethylamine.

Workup

  1. concentrationwas concentrated
  2. dissolutiondissolved in water
  3. washwashed with diethyl ether
  4. extractionextracted with diethyl ether
  5. dry with materialThe ethereal layer was dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. custompurified by silica chromatography

Sources & evidence

ORD record
ord-1938a09594ac48bc91916ee5c7d5380d
Source dataset
uspto-grants-1992_04
Patent number
US05106839

Reaction notes

Loading…