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

HRID 2419144Notes

Reaction equation

HRID 2419144 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 2.98 g 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 four 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 four days
  2. filtrationThe reaction mixture is filtered while hot, and the solid
  3. customis collected
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-feda2da6920f41aeb1a15ecdf46c5539
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

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