Phenylacetaldehyde → 3-(1,3-Benzodithiol-2-ylideneamino)-5-(2-phenylethylidene)-2-thioxo-4-thiazolidinone

HRID 2419569Notes

Reaction equation

HRID 2419569 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:18]1([CH2:24][CH:25]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>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:25][CH2:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:13][C:12]1=[S:17]

Participants

5

Reactant 2

HCID 998PhenylacetaldehydeHCID 124949933-[(1,3-Benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone

Product 1

HCID 739981023-(1,3-Benzodithiol-2-ylideneamino)-5-(2-phenylethylidene)-2-thioxo-4-thiazolidinone

Reagents, catalysts & solvents 2

HCID 9793820Piperidine, acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A slurry of 2.98g of 3-[(1,3-benzodithiol-2-ylidene)amino] -2-thioxo-4-thiazolidinone (see example 37), phenylacetaldehyde (10 ml, excess) and acetic acid/piperidine (10 drops) in 600 ml of anhydrous glyme is heated at reflux for 4 days. The reaction mixture is filtered while hot, and the solid is collected and recrystallized from dimethylformamide to yield 1.78 g of the title compound, melting point 233°-234° C.

Workup

  1. temperatureat reflux for 4 days
  2. filtrationThe reaction mixture is filtered while hot, and the solid
  3. customis collected
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-a77cef40f68a487f8dfcc0e2bee35980
Source dataset
uspto-grants-1978_08
Patent number
US04107175

Reaction notes

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