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

HRID 2419567Notes

Reaction equation

HRID 2419567 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]>C(O)(=O)C.N1CCCCC1.C(=O)CCCC>[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:6][CH2:5][CH2:4][CH2:9][CH3:8])[S:13][C:12]1=[S:17]

Participants

4

Reactant 1

HCID 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-thiazolidinoneYield 89.6%

Reagents, catalysts & solvents 2

HCID 9793820Piperidine, acetateCatalystHCID 8063PentanalSolvent

Procedure

A slurry of 2.0g 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 slyme (400 ml) is heated at reflux for eighteen 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 eighteen 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-ee6cda9cab894396a20a06a768418928
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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