Octanal → 3-[(1,3-Benzodithiol-2-ylidene)amino]-5-octylidene-2-thioxo-4-thiazolidinon

HRID 2419143Notes

Reaction equation

HRID 2419143 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][N:11]1[C:15](=[O:16])[CH2:14][S:13][C:12]1=[S:17].[CH:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)(=O)C.N1CCCCC1.C(COC)OC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[S:3][C:2]1=[N:10][N:11]1[C:15](=[O:16])[C:14](=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[S:13][C:12]1=[S:17]

Participants

5

Reactant 2

HCID 454OctanalHCID 124949933-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone

Product 1

HCID 736760703-[(1,3-Benzodithiol-2-ylidene)amino]-5-octylidene-2-thioxo-4-thiazolidinon

Reagents, catalysts & solvents 2

HCID 9793820Piperidine, acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A slurry of 2.0 g of 3-[(1,3-benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone (see example 37), octanal (15 ml, excess) and acetic acid/piperidine (10 drops) in anhydrous glyme (400 ml) is heated at reflux for 18 hours. The reaction mixture is chilled in an ice bath and the resultant precipitate collected by filtration. The precipitate is recrystallized twice from dimethylformamide to yield 1.02 g of the title compound, melting point 185° C.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction mixture is chilled in an ice bath
  3. filtrationthe resultant precipitate collected by filtration
  4. customThe precipitate is recrystallized twice from dimethylformamide

Sources & evidence

ORD record
ord-376d3a797d6a44048998377418556a2e
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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