Triethylamine → HCID 14822254, compound

HRID 1614560Notes

Reaction equation

HRID 1614560 reaction equation
[S:1]1[CH2:5][CH2:4][NH:3][CH2:2]1.C(N(CC)CC)C.[C:13]1([CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:13]1([CH2:19][CH2:20][CH2:21][C:22]([N:3]2[CH2:4][CH2:5][S:1][CH2:2]2)=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10444ThiazolidineHCID 117898654-Phenylbutanoyl Chloride

Product 1

HCID 14822254HCID 14822254, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.5 mmol of thiazolidine and 5.5 mmol of triethylamine were dissolved in 10 ml of methylene chloride. To the solution 5 mmol of 4-phenylbutanoyl chloride was added dropwise under ice-cooling with stirring. The mixture was left to raise to room temperature and further heated under refluxing for 2 hours. The resulting reaction mixture was washed with 1N hydrochloric acid, brine, and saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated by distillation and the residue was purified by column chromatography on silica gel to obtain 1.14 g of colorless crystals of N-(4-phenylbutanoyl)thiazolidine (yield: 88%).

Workup

  1. temperaturecooling
  2. waitThe mixture was left
  3. temperaturefurther heated
  4. temperatureunder refluxing for 2 hours
  5. customThe resulting reaction mixture
  6. washwas washed with 1N hydrochloric acid, brine, and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated by distillation
  9. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ed6c3d1b481a44c690173f71a8ee6db0
Source dataset
uspto-grants-1993_03
Patent number
US05198450

Reaction notes

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