Dimethylamine → HCID 14999116, compound

HRID 1493246Notes

Reaction equation

HRID 1493246 reaction equation
[CH3:1][NH:2][CH3:3].Cl[CH2:5][CH2:6][N:7]1[C:11](=[O:12])[CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[S:9][CH:8]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>CS(C)=O>[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][N:7]1[C:11](=[O:12])[CH:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[S:9][CH:8]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 14999113HCID 14999113, compound

Product 1

HCID 14999116HCID 14999116, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A 50% aqueous dimethylamine solution (1.0 ml, 11 mmol) was added to a solution of trans-isomer (128 mg, 0.35 mmol) of 3-(2-chloroethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one in dimethylsulfoxide (3 ml). The mixture, placed in a sealed tube, was heated at 100° C. for hours. After removal of the solvent by evaporation under reduced pressure, the residue was dissolved in chloroform (30 ml). The solution was washed twice with saturated aqueous NaHCO3 and dried. Removal of the chloroform gave the intended trans-isomer (131 mg, quantitative yield) of 3-(2-dimethylaminoethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one as an oily form.

Workup

  1. customThe mixture, placed in a sealed tube
  2. customAfter removal of the solvent
  3. customby evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform (30 ml)
  5. washThe solution was washed twice with saturated aqueous NaHCO3
  6. customdried
  7. customRemoval of the chloroform

Sources & evidence

ORD record
ord-caec91a6f09e4ca7b6ce0f2bf2da8ece
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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