2,3-Dichlorobenzaldehyde → 5-[(2,3-Dichlorophenyl)methylene]-2-thioxo-4-thiazolidinone

HRID 247865Notes

Reaction equation

HRID 247865 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[S:11]1[CH2:17][C:15](=[O:16])[NH:14][C:12]1=[S:13].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:17]1[S:11][C:12](=[S:13])[NH:14][C:15]1=[O:16]

Participants

5

Reactant 3

HCID 357452,3-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 28543725-[(2,3-Dichlorophenyl)methylene]-2-thioxo-4-thiazolidinoneYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2,3-dichlorobenzaldehyde (4.6 g, 26 mmoles), rhodanine (3.5 g, 25 mmoles), sodium acetate (7.5 g, 91 mmoles), and acetic acid (40 ml) is stirred under an inert atmosphere and heated to reflux. After 2.5 hours the mixture is stirred into ice-water (250 ml) and the precipitate is filtered off, rinsed three times with water and dried. Recrystallization from methanol gave the pure product (2.9 g), mp 203°-204° C.

Workup

  1. temperatureheated to reflux
  2. filtrationthe precipitate is filtered off
  3. washrinsed three times with water
  4. customdried
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-6e8fa67b6ed14514bfa4c58170aa89bc
Source dataset
uspto-grants-1993_05
Patent number
US05208250

Reaction notes

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