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

HRID 517587Notes

Reaction equation

HRID 517587 reaction equation
NCC[N:4]1C(=O)/[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:23]([CH2:26]C)[CH2:24][CH3:25])C.[CH2:28]=[O:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:26][N:23]([CH3:21])[CH2:24][CH2:25][N:4]1[C:28](=[O:29])/[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]

Participants

6

Reactant 4

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

Product 1

HCID 45485994(Z)-3-(2-(dimethylamino)ethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneYield 76.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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 24a (76.2%, 73 mg) as a yellow solid.

Workup

  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

Sources & evidence

ORD record
ord-26900104a4f54aeea51f6ebbd1ed3f0e
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

Loading…