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

HRID 373502

Reaction equation

HRID 373502 reaction equation
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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c56d0b680bf74a5684a5042b40c5b1ef
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Linked notes

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