Acetic Anhydride → (Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

HRID 517589Notes

Reaction equation

HRID 517589 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20].C(N(CC)CC)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>ClCCl>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11](/[CH:10]=[C:7]2/[C:8](=[O:9])[N:4]([CH2:3][CH2:2][NH:1][C:28](=[O:30])[CH3:29])[C:5](=[O:20])[S:6]/2)=[CH:12][CH:13]=1)[CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Product 1

HCID 45485995(Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamideYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 76 (101 mg, 0.25 mmol) in 5 mL of dichloromethane was added triethylamine (105 μL, 0.75 mmol) and acetic anhydride (26.0 μL, 0.28 mmol). After being stirred at room temperature overnight, the reaction solution was diluted with 50 mL of dichloromethane, washed with water, collected the organic layer, dried over Na2SO4, filtered, concentrated and purified by silica column chromatography (33% dichloromethane in ethyl acetate) to afford 74 mg (88.6%) of the title compound 25a as a light-yellow solid.

Workup

  1. washwashed with water
  2. customcollected the organic layer
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica column chromatography (33% dichloromethane in ethyl acetate)

Sources & evidence

ORD record
ord-09a94cdb5ea44a67a36ffaf1f42536b7
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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