Sodium Chloride → HCID 14999116, compound

HRID 1030565Notes

Reaction equation

HRID 1030565 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.[CH3:8][N:9]([CH3:13])[CH2:10][CH2:11]Cl.[CH2:14]([CH:23]1[S:27][CH:26]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[NH:25][C:24]1=[O:34])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Na+].[Cl-]>CN(C)C=O>[CH3:8][N:9]([CH3:13])[CH2:10][CH2:11][N:25]1[C:24](=[O:34])[CH:23]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[S:27][CH:26]1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 14649072HCID 14649072, compound

Product 1

HCID 14999116HCID 14999116, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (0.9 g, 6.52 mmol) and 2-dimethylaminoethyl chloride hydrochloride (0.47 g, 3.26 mmol) were added to a solution of 5-(n-nonyl)-2-(3-pyridyl)-thiazolidin-4-one (1 g, 3.26 mmol) in dry dimethylformamide (10 ml). The mixture was kept at 50° C. for 10 hours. The resulting mixture, after addition of aqueous NaCl, was extracted with ethyl acetate. The extract was washed with aqueous NaCl, dried, and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel, giving 3-(2-dimethylaminoethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one (0.41 g, 33% yield). IR (CHCl3) [cm-1 ]; 2850, 1660, 1578, 1407.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with aqueous NaCl
  3. customdried
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-89470ac60265465390f0831c19d8b4e4
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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