Maleic Anhydride → HCID 67867837, compound

HRID 1638293Notes

Reaction equation

HRID 1638293 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.[C:22]1(=[O:28])[O:27][C:25](=[O:26])[CH:24]=[CH:23]1>N1C=CC=CC=1.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:15][CH2:16][CH:17]([O:20][C:22]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[O:28])[CH2:18][CH2:19]3)=[O:13])[C:6]=2[CH:21]=1

Participants

5

Reactant 2

HCID 7923Maleic AnhydrideHCID 3082453Hpr 611

Product 1

HCID 67867837HCID 67867837, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-chloro-3-(4-hydroxypiperidinocarbonylmetyl)benzothiazolin-2-one (3.2 g) in dry pyridine (2.5 ml) and dry tetrahydrofuran (50 ml) was cooled, to which a solution of maleic anhydride (1.0 g) in dry tetrahydrofuran (5 ml) was gradually dropwise added under stirring. The mixture was refluxed for two hours and then left overnight. The solvent was evaporated off under vacuum from the reaction mixture, and the residue was dissolved in 5% aqueous sodium bicarbonate (20 ml). The solution was cooled and adjusted to pH 2 with 1% hydrochloric acid. The precipitated crystals were collected by filtration, washed with water and then subjected to chromatography on silica gel eluting with ethanol/benzene (1:1). The solvent was evaporated off under vacuum from the eluate at below 50° C. The residue was recrystallized from isopropyl alcohol to yield the title compound as colorless crystals (2.1 g). m.p. 197°-198° C.

Workup

  1. additionwas gradually dropwise added
  2. temperatureThe mixture was refluxed for two hours
  3. customThe solvent was evaporated off under vacuum from the reaction mixture
  4. dissolutionthe residue was dissolved in 5% aqueous sodium bicarbonate (20 ml)
  5. temperatureThe solution was cooled
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customThe solvent was evaporated off under vacuum from the eluate at below 50° C
  9. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-ddc001b8c45d46b593853b708261050a
Source dataset
uspto-grants-1989_11
Patent number
US04879301

Reaction notes

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