1-CHLORO-1-ETHENESULFONYL CHLORIDE → HCID 57588282, compound

HRID 1782089Notes

Reaction equation

HRID 1782089 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]=[N+:16]=[N-:17])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8].[Cl:19][C:20](S(Cl)(=O)=O)=[CH2:21]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:21]=[C:20]([Cl:19])[N:17]=[N:16]3)[O:11][C:10]2=[O:18])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

4

Reactant 2

HCID 102613831-CHLORO-1-ETHENESULFONYL CHLORIDEHCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 57588282HCID 57588282, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-azidomethyl-1,3-oxazolidin-2-one (1 g, 28 mmol) and 1-chloro-1-ethenesulfonyl chloride (1 g, 6.2 mmol) was heated in a pressure tube at 80° C. for one hour. The reaction mixture was cooled to room temperature, diluted with chloroform (15 mL), and heated at 80° C. for an additional 4 hours. The reaction mixture was cooled to room temperature and the precipitate was collected by filtration and washed with little dichloromethane to yield the title compound as a colorless amorphous solid (725 mg, 62%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureheated at 80° C. for an additional 4 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with little dichloromethane

Sources & evidence

ORD record
ord-edac06a9f1bc42bead9591b4140e9181
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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