Sodium Chloride → HCID 14999116, compound

HRID 981562Notes

Reaction equation

HRID 981562 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5]Cl.[CH2:8]([CH:17]1[S:21][CH:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[NH:19][C:18]1=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[Na+].[Cl-]>CN(C)C=O>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][N:19]1[C:18](=[O:28])[CH:17]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[S:21][CH:20]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

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

Product 1

HCID 14999116HCID 14999116, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2C03 (0 9 g, 6.52 mmol) and 2-dimethylamino-ethyl 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 dimethylform-amide (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).

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-e2c8b0ae27854ffcb5236414faabe506
Source dataset
uspto-grants-1991_02
Patent number
US04992455

Reaction notes

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