Formaldehyde → 2,4-Thiazolidinedione, 3-[[(2-methylphenyl)amino]methyl]-

HRID 2418942Notes

Reaction equation

HRID 2418942 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:9]=O.[S:11]1[CH2:15][C:14](=[O:16])[NH:13][C:12]1=[O:17]>C(O)C>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:9][N:13]1[C:14](=[O:16])[CH2:15][S:11][C:12]1=[O:17]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5437ThiazolidinedioneHCID 7242O-Toluidine

Product 1

HCID 28441932,4-Thiazolidinedione, 3-[[(2-methylphenyl)amino]methyl]-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10.7 g of o-toluidine, 3.3 g. of paraformaldehyde, and 11.7 g of 2,4-thiazolidinedione in 100 ml of absolute ethanol was refluxed 5 hrs under nitrogen atmosphere. On cooling, the resulting precipitate was filtered off to give 22.1 g of N-(2-methylphenylaminomethyl)-2,4-thiazolidinedione, mp 109°-111° C; identified by IR and NMR.

Workup

  1. temperatureOn cooling
  2. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-e06e13261199457e9cc9c5c423605b83
Source dataset
uspto-grants-1978_08
Patent number
US04104051

Reaction notes

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