Acetic Anhydride → HCID 19820663, compound

HRID 1030566Notes

Reaction equation

HRID 1030566 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[S:13][CH:12]1[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[C:1]([NH:8][CH2:9][CH2:10][N:11]1[C:15](=[O:16])[CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[S:13][CH:12]1[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 19820668HCID 19820668, compound

Product 1

HCID 19820663HCID 19820663, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.2 g) was added dropwise to a solution of 3-(2-aminoethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one (0.50 g, 1.43 mmol) in pyridine (2 ml) with stirring under cooling with ice. The mixture was left standing overnight at room temperature. To this solution was added saturated aqueous NaHCO3 (30 ml), and the mixture was extracted with benzene. After drying of the extract, the solvent was removed therefrom by evaporation under reduced pressure, giving the intended 3-(2-acetylaminoethyl)-5-(n-nonyl)-2-(3-pyridyl)thiazolidin-4-one (0.52 g, 92% yield) in oily form. IR (CHCl3) [cm-1 ]; 3430, 2920, 2850, 1665, 1590, 1580, 1365. NMR (δ, CDCl3 ppm); 1.95 (3 H, s), 3.93 (0.45 H, dd, 990 and 3.63 Hz), 4.03 (0.55 H, ddd, 9.24, 3.63 and 1.65 Hz), 5,75 (0.55 H, d, 1.65 Hz), 5.76 (0.45 H, s), 6.06-6.11 (1 H, m).

Workup

  1. temperatureunder cooling with ice
  2. waitThe mixture was left
  3. extractionthe mixture was extracted with benzene
  4. customAfter drying of the extract
  5. customthe solvent was removed
  6. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-2b273b2b45ac4d48a5de95467eddc559
Source dataset
uspto-grants-1992_04
Patent number
US05106860

Reaction notes

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