Sodium Chloride → HCID 14999116, compound

HRID 1493244Notes

Reaction equation

HRID 1493244 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, 0.41 g, 33% yield).

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-fca6a52e15f143e6b66f60e81b59b2cd
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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