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3,4-Dichlorobenzaldehyde → 5-[(3,4-Dichlorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

HRID 2086915
Notes
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Reaction equation

HRID 2086915 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[S:3].[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[Cl:17])[CH:12]=O.C([O-])(=O)C.[Na+]>CO>[Cl:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:7]2[S:1][C:2](=[S:3])[NH:4][C:5]2=[O:6])[CH:14]=[CH:15][C:16]=1[Cl:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 1201546Rhodanine

Product 1

HCID 27969505-[(3,4-Dichlorophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A 50 mL flask was charged with 899 mg rhodanine (6.75 mmol, 1.0 equiv), 1.77 g 3,4-dichlorobenzaldehyde (10.1 mmol, 1.5 equiv), 1.66 g sodium acetate (20.25 mmol, 3.0 equiv) and 20 mL methanol. The mixture was heated to 65° C. with stirring for 1.75 h. The yellow solid was then filtered and washed (4×MeOH) to give the product 5-(3,4-dichlorophenylmethylene)-4-oxo-2-thionothiazolidine as a yellow solid (1.059 g 3.67 mmol, 54%).

Workup

  1. filtrationThe yellow solid was then filtered
  2. washwashed (4×MeOH)

Sources & evidence

ORD record
ord-8493600ae1e948e4b9d8a506781b9b84
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06727267B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes