Thionyl Chloride → (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride

HRID 373502

Reaktionsgleichung

Reaktionsgleichung von HRID 373502
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[C:8]2[C@:15]3([C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]3)[CH2:14][C@@H:13]([C:22]([OH:24])=O)[O:12][C:9]2=[CH:10][CH:11]=1>>[F:5][C:6]1[CH:7]=[C:8]2[C@:15]3([C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]3)[CH2:14][C@@H:13]([C:22]([Cl:3])=[O:24])[O:12][C:9]2=[CH:10][CH:11]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 9838583(2S,4S)-6-Fluoro-2,3-dihydro-2',5'-dioxospiro(4H-1-benzopyran-4,4'-imidazolidine)-2-carboxylic acid

Produkt 1

HCID 57210646(2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride

Versuchsvorschrift

To thionyl chloride (24.9 ml, 3.57 mol) was added (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxylic acid (20.0 g, 71.4 mmol). After refluxing the mixture under argon atmosphere for 22 hours, the excess thionyl chloride was evaporated in vacuo to dryness to give quantitatively crude crystals of (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carbonyl chloride.

Aufarbeitung

  1. temperatureAfter refluxing the mixture under argon atmosphere for 22 hours
  2. customthe excess thionyl chloride was evaporated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c56d0b680bf74a5684a5042b40c5b1ef
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05164391

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