Succinic anhydride → HCID 14601655, compound

HRID 1638291Notes

Reaction equation

HRID 1638291 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][CH2:17][CH:16]([OH:20])[CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.[C:22]1(=[O:28])[O:27][C:25](=[O:26])[CH2:24][CH2:23]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[CH2:19][CH2:18][CH2:17][CH:16]([O:20][C:22]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:28])[CH2:15]3)=[O:13])[C:6]=2[CH:21]=1

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 14601654HCID 14601654, compound

Product 1

HCID 14601655HCID 14601655, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-chloro-3-(3-hydroxypiperidinocarbonylmethyl)benzothiazolin-2-one (3.2 g) in dry pyridine (2.5 ml) and dry tetrahydrofuran (50 ml) was cooled. To the solution was dropwise added a solution of succinic anhydride (1.1 g) in dry tetrahydrofuran (5 ml) under stirring. The mixture was refluxed for two hours and then left overnight. The solvent was evaporated off under vacuum from the reaction mixture. The residue was dissolved in 5% aqueous sodium bicarbonate (20 ml). The resultant solution was cooled and adjusted to pH 2 with 1% hydrochloric acid. The precipitated crystals were collected by filtration, washed with water and then recrystallized from isopropyl alcohol to yield the title compound as colorless crystals (2.0 g). m.p. 131°-133° C.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. customThe solvent was evaporated off under vacuum from the reaction mixture
  3. dissolutionThe residue was dissolved in 5% aqueous sodium bicarbonate (20 ml)
  4. temperatureThe resultant solution was cooled
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-f32775942a674ecab523e866f7a795d3
Source dataset
uspto-grants-1989_11
Patent number
US04879301

Reaction notes

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