4-Hydroxybenzaldehyde → (Z)-3-(2-aminoethyl)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione

HRID 517617

Reaction equation

HRID 517617 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C([NH:29][CH2:30][CH2:31][N:32]1[C:36](=[O:37])[CH2:35][S:34][C:33]1=[O:38])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.N1CCCCC1.NCCN1C(=O)/C(=C/C2C=CC=CC=2)/SC1=O>>[NH2:29][CH2:30][CH2:31][N:32]1[C:36](=[O:37])/[C:35](=[CH:6]/[C:5]2[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=2)/[S:34][C:33]1=[O:38]

Participants

5

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 15512443-(2-Aminoethyl)-5-(phenylmethylidene)-1,3-thiazolidine-2,4-dioneHCID 716971683-(2-(Tritylamino)ethyl)thiazolidine-2,4-dione

Product 1

HCID 43145551(Z)-3-(2-aminoethyl)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione

Procedure

The title compound 30f was prepared from 4-hydroxybenzaldehyde (76 mg, 0.62 mmol), compound 29 (250 mg, 0.62 mmol) and piperidine (20.0 μL, 0.19 mmol) in a manner similar to that described for 30a in 43.0% (102 mg) yield as a yellow solid.

Workup

  1. customyield as a yellow solid

Sources & evidence

ORD record
ord-ee07d70468a04974beb700f8edfe3186
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Linked notes

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