Prolinol → HCID 14441886, compound

HRID 654397Notes

Reaction equation

HRID 654397 reaction equation
O[CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.[Cl:8][C:9]1[C:14]([O:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][C:12]([N:20]=[C:21]=[S:22])=[C:11]([F:23])[CH:10]=1>O1CCOCC1>[Cl:8][C:9]1[C:14]([O:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][C:12]([N:20]=[C:21]2[N:4]3[CH2:5][CH2:6][CH2:7][CH:3]3[CH2:2][S:22]2)=[C:11]([F:23])[CH:10]=1

Participants

4

Reactant 2

HCID 90908ProlinolHCID 14441885HCID 14441885, compound

Product 1

HCID 14441886HCID 14441886, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10 g 2-(Hydroxymethyl)pyrrolidine and 27.6 g 4-chloro-2-fluoro-5-methylsulphonyloxyphenyl isothiocyanate were heated under reflux for 4 hours in 200 ml dioxane. The solvent was removed and the residue heated with 50 ml 48% hydrobromic acid. After cooling, the reaction solution was added to an ice/water mixture, neutralised with 40% caustic soda and extracted with methylene chloride. After drying and concentrating, the crude product was purified by column chromatography (silica gel, eluent; hexane/ethyl acetate).

Workup

  1. customThe solvent was removed
  2. temperaturethe residue heated with 50 ml 48% hydrobromic acid
  3. temperatureAfter cooling
  4. additionthe reaction solution was added to an ice/water mixture
  5. extractionextracted with methylene chloride
  6. customAfter drying
  7. concentrationconcentrating
  8. customthe crude product was purified by column chromatography (silica gel, eluent; hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c867542672dd499599ac5aca326a3104
Source dataset
uspto-grants-1992_07
Patent number
US05131946

Reaction notes

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