Benzaldehyde → 3-Benzyl-5-benzylidene-2-sulfanylidene-1,3-thiazolidin-4-one

HRID 600831Notes

Reaction equation

HRID 600831 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][S:10][C:9]1=[S:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[CH2:1]([N:8]1[C:12](=[O:13])[C:11](=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:10][C:9]1=[S:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 976733-(Phenylmethyl)-2-thioxo-4-thiazolidinone

Product 1

HCID 2116353-Benzyl-5-benzylidene-2-sulfanylidene-1,3-thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-benzylrhodanine (0.50 g, 2.2 mmol), benzaldehyde (0.23 mL, 2.3 mmol) and TEA (0.68 mL, 4.9 mmol) in MeCN (5 mL, anhyd) was heated at reflux. After 2 h the reaction mixture was cooled. Precipitated solids were collected by filtration, triturated with MeCN-Hex and dried under vacuum to yield 3-benzyl-5-benzylidene-2-thioxothiazolidin-4-one, which was used without further purification.

Workup

  1. temperatureanhyd) was heated
  2. temperatureat reflux
  3. temperatureAfter 2 h the reaction mixture was cooled
  4. customPrecipitated solids
  5. filtrationwere collected by filtration
  6. customtriturated with MeCN-Hex
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6375490ab34540f08e3287c6fc1faa34
Source dataset
uspto-grants-2011_03
Patent number
US07902237B2

Reaction notes

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