Dimethylamine → HCID 14999116, compound

HRID 1030567Notes

Reaction equation

HRID 1030567 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 100%

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 2 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, 100% of theoretical) of 3-(2-dimethylaminoethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one in oily form. IR (CHCl3) [cm-1 ]; 2930, 2860, 1670, 1580, 1355. NMR (δ, CDCl3, ppm); 2.15 (6 H, s), 2.24 (1 H, dt, 12.87 and 5.61 Hz), 2.46 (1 H, ddd, 12.87, 7.20 and 5.94 Hz), 2.69 (1 H, ddd, 14.19, 7.20 and 5.61 Hz), 3.80 (1 H, ddd, 14.19, 5.94 and 5.61 Hz), 4.03 (1 H, ddd, 8.58, 3.96 and 1.98 Hz), 5.86 (1 H, d, 1.98 Hz).

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-d08fdc42f317426c9230da47acd2740b
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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