Chloroform → Triethylamine, 2,2'-dichloro-2-phenoxy-, hydrochloride

HRID 655594Notes

Reaction equation

HRID 655594 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5]CO.S(Cl)([Cl:19])=O.[CH:21]([Cl:24])(Cl)Cl>>[ClH:19].[Cl:19][CH2:2][CH2:3][N:4]([CH2:5][CH2:21][Cl:24])[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 11770129HCID 11770129, compound

Product 1

HCID 3025297Triethylamine, 2,2'-dichloro-2-phenoxy-, hydrochloride

Procedure

To an ice-cold solution of 2-[(2-hydroxyethyl)-(2-phenoxyethyl)-amino]ethanol (H, 43.9 g, 194 mmol) in chloroform (140 mL) was added thionyl chloride (SOCl2; 114.8 g, 965 mmol) dropwise. The reaction mixture was then reflux for 1.5 h and concentrated. The residue was then suspended in the mixture of ethyl acetate and isopropyl ether. The precipitate was filtered and dried in a vacuum oven to afford the title compound quantitatively as a light brown crystal. This product was then used without further purification.

Workup

  1. temperatureThe reaction mixture was then reflux for 1.5 h
  2. concentrationconcentrated
  3. additionThe residue was then suspended in the mixture of ethyl acetate and isopropyl ether
  4. filtrationThe precipitate was filtered
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-704fc6fb168e423a9821b2a862d231c6
Source dataset
uspto-grants-2011_12
Patent number
US08071602B2

Reaction notes

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