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

HRID 373503

Reaction equation

HRID 373503 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 chlorideYield 100%

Procedure

To thionyl chloride (400 ml, 5.11 mol) was added (2S,4S)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxylic acid (20.0 g, 67.1 mmol). After refluxing the mixture for 18 hours, the resulting reaction mixture was dried in vacuo to dryness to give the desired compound (20.0 g, 100%).

Workup

  1. temperatureAfter refluxing the mixture for 18 hours
  2. customthe resulting reaction mixture
  3. customwas dried in vacuo to dryness

Sources & evidence

ORD record
ord-ec34fe252f0d41e0a8734a7c725b0b7a
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Linked notes

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