2-Methyl-1,3-thiazolidine → HCID 19905282, compound

HRID 2371867Notes

Reaction equation

HRID 2371867 reaction equation
[CH:1]1[C:6]([C:7]([CH2:9][CH2:10]Cl)=[O:8])=[CH:5][CH:4]=[C:3]([F:12])[CH:2]=1.[CH3:13][CH:14]1[NH:18][CH2:17][CH2:16][S:15]1.C([O-])(=O)C.[Na+]>C(O)C>[F:12][C:3]1[CH:4]=[CH:5][C:6]([C:7](=[O:8])[CH2:9][CH2:10][N:18]2[CH2:17][CH2:16][S:15][CH:14]2[CH3:13])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 321962-Methyl-1,3-thiazolidineHCID 676722-Chloro-4'-fluoropropiophenoneHCID 517045Sodium Acetate

Product 1

HCID 19905282HCID 19905282, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.73 g (0.02 mol) of β-chloro-4-fluoropropiophenone are added in little portions at room temperature to a suspension containing 2.06 g (0.02 mol) of 2-methylthiazolidine and 1.64 g (0.02 mol) of anhydrous sodium acetate in 20 ml of ethanol over 30 minutes under stirring. After stirring for an additional 3 hours, the reaction mixture is evaporated, saturated sodium hydrogen carbonate solution is added to the oily yellow residue and it is extracted twice with 30 ml of ether each. After drying and evaporating the extract, the oily yellow residue is dissolved in acetone and acidified by 48% hydrobromic acid. Thus, 4.26 g of a white crystalline product are obtained and recrystallized twice from ethanol to give 2.00 g (29.9%) of hydrobromide of the title compound, m.p.: 151°-152° C.

Workup

  1. stirringAfter stirring for an additional 3 hours
  2. customthe reaction mixture is evaporated
  3. additionsaturated sodium hydrogen carbonate solution is added to the oily yellow residue and it
  4. extractionis extracted twice with 30 ml of ether each
  5. customAfter drying
  6. customevaporating the extract
  7. dissolutionthe oily yellow residue is dissolved in acetone

Sources & evidence

ORD record
ord-cef2e62477e64803843e1171c57e1ad6
Source dataset
uspto-grants-1992_03
Patent number
US05096902

Reaction notes

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