Thionyl Chloride → HCID 22386181, compound

HRID 895271Notes

Reaction equation

HRID 895271 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[O:10][CH2:11][C:12](O)=[O:13])[CH3:6]>>[CH2:5]([O:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[O:10][CH2:11][C:12]([Cl:3])=[O:13])[CH3:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 351531(2-Ethoxy-phenoxy)-acetic acid

Product 1

HCID 22386181HCID 22386181, compound

Procedure

1.30 g (11 mmol) of thionyl chloride was added to 1.96 g (10 mmol, 1.0 eq.) of (2-ethoxy-phenoxy)acetic acid. The mixture was heated under reflux for 30 minutes and distilled under reduced pressure to obtain (2-ethoxy-phenoxy)acetyl chloride. 20 ml of THF and 2.78 ml (20 mmol, 2.0 eq.) of triethylamine were added to 2.44 g (10 mmol, 1.0 eq.) of (R)-(-)-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzene sulfonamide and the reaction solution was cooled down to 0° C. The obtained (2-ethoxy-phenoxy)acetyl chloride was added dropwise thereto and the whole mixture was stirred for 1 hour. The formed solids were filtered, and the filtrate was distilled under reduced pressure and extracted with 40 ml of ethyl acetate. Subsequently, the extract was washed with 1 N HCl, a saturated aqueous solution of sodium bicarbonate and brine, and dried over magnesium sulfate and then, filtered. The filtrate was distilled under reduced pressure to obtain 3.80 g (yield: 90%) of 2-(2-ethoxy-phenoxy)-N-[2-(4-methoxy-3-sulfamoyl-phenyl)-1-methyl-ethyl]-acetamide.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-afd4dffd390d41118b5fb819fa6cab2e
Source dataset
uspto-grants-2005_07
Patent number
US06914159B1

Reaction notes

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