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

HRID 128727

Reaction equation

HRID 128727 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, 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-029bb7e8f5a3430fb8eff75b0d44cb04
Source dataset
uspto-grants-1995_11
Patent number
US05464856

Linked notes

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