Formaldehyde → (Z)-5-(4-ethoxybenzylidene)-3-(2-(methylamino)ethyl)thiazolidine-2,4-dione

HRID 517584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517584
[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].[CH2:21](N(CC)CC)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[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][CH3:21])[C:5](=[O:20])[S:6]/2)=[CH:12][CH:13]=1)[CH3:19]

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 71697257(Z)-5-(4-ethoxybenzylidene)-3-(2-(methylamino)ethyl)thiazolidine-2,4-dioneAusbeute 38,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 76 (122 mg, 0.30 mmol) in 4 mL of 1,2-dichloroethane was added triethylamine (84 μL, 0.60 mmol), aqueous formaldehyde (37%, 24 μL, 0.30 mmol) and sodium triacetoxyborohydride (254 mg, 1.20 mmol). The reaction mixture was allowed to stir overnight at room temperature. The reaction was quenched by adding sat'd aqueous NaHCO3 and stirred at room temperature for 20 min. The reaction mixture was partitioned between ethyl acetate and sat'd aqueous NaHCO3, the organic layer was washed with brine, collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography using dichloromethane/methanol/NH4OH (ratio: 92/7/1) to afford compound 23a (38.1%, 35 mg) as a yellow solid.

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby adding sat'd aqueous NaHCO3
  3. stirringstirred at room temperature for 20 min
  4. customThe reaction mixture was partitioned between ethyl acetate
  5. washthe organic layer was washed with brine
  6. customcollected
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dc365044d74b4e7dba41c15e2b90044c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115122B2

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