Benzaldehyde → 3-(2-Aminoethyl)-5-(phenylmethylidene)-1,3-thiazolidine-2,4-dione

HRID 517612

Reaction equation

HRID 517612 reaction equation
C(=O)C1C=CC=CC=1.C(NCCN1C(=O)CSC1=O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.N1CCCCC1.[NH2:44][CH2:45][CH2:46][N:47]1[C:51](=[O:52])[CH:50]([CH2:53][C:54]2[CH:59]=[CH:58][C:57](OCC)=[CH:56][CH:55]=2)[S:49][C:48]1=[O:63]>C(O)C>[NH2:44][CH2:45][CH2:46][N:47]1[C:51](=[O:52])/[C:50](=[CH:53]/[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)/[S:49][C:48]1=[O:63]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8082PiperidineHCID 716970713-(2-Aminoethyl)-5-(4-ethoxybenzyl)thiazolidine-2,4-dioneHCID 716971683-(2-(Tritylamino)ethyl)thiazolidine-2,4-dione

Product 1

HCID 15512443-(2-Aminoethyl)-5-(phenylmethylidene)-1,3-thiazolidine-2,4-dioneYield 48.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

Benzaldehyde (63 μL, 0.62 mmol) and compound 29 (250 mg, 0.62 mmol) were dissolved in 10 mL of anhydrous ethanol at room temperature, and piperidine (7 μL, 0.062 mmol) was added to the reaction solution. The reaction mixture was stirred at 75° C. for 1 day and then allowed to cool down to room temperature until a yellow crystalline precipitate formed, and the solid was collected by filtration, washed with water and ethyl acetate, and dried to afford a white solid. Deprotection following the procedure of compound 6 gave the title compound 30a as a white solid (48.1%, 74 mg).

Workup

  1. temperatureto cool down to room temperature until a yellow crystalline precipitate
  2. customformed
  3. filtrationthe solid was collected by filtration
  4. washwashed with water and ethyl acetate
  5. customdried
  6. customto afford a white solid

Sources & evidence

ORD record
ord-1c0a01a673f2498fba074e97cbe46588
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Linked notes

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