Pentanal → 3-[(1,3-Benzodithiol-2-ylidene)amino]-5-pentylidene-2-thioxo-4-thiazolidinone

HRID 2419142Notes

Reaction equation

HRID 2419142 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][CH3:22]>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][CH3:22])[S:13][C:12]1=[S:17]

Participants

5

Reactant 2

HCID 8063PentanalHCID 124949933-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone

Product 1

HCID 573245323-[(1,3-Benzodithiol-2-ylidene)amino]-5-pentylidene-2-thioxo-4-thiazolidinone

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), valeraldehyde (10 ml, excess) and acetic acid/piperidine (2:1) (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. This precipitate (1.6 g) is recrystallized from 50 ml of dimethylformamide to yield 1.1 g of the title compound, melting point 210°-212° 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. customThis precipitate (1.6 g) is recrystallized from 50 ml of dimethylformamide

Sources & evidence

ORD record
ord-d76bac9241844250b37dd378a76acef2
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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