Acetic Acid → 5-(2-Fluoro-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one

HRID 1822950Notes

Reaction equation

HRID 1822950 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.[S:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[S:14].C(O)(=O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[NH4+]>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[C:18]1[S:12][C:13](=[S:14])[NH:15][C:16]1=[O:17]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 1201546RhodanineHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 850594845-(2-Fluoro-5-methoxybenzylidene)-2-thioxo-1,3-thiazolidin-4-oneYield 91.5%

Reagents, catalysts & solvents 2

HCID 517165Ammonium AcetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-fluoro-5-methoxybenzaldehyde (5.00 g, 32.46 mmol) and rhodanine (4.31 g, 32.46 mmol) in dry toluene (1000 mL) was added ammonium acetate (50 mg) and acetic acid (2 mL). The resulting suspension was allowed to stir at 120° C. for 12 h under Dean-Stark apparatus before being allowed to cool and filtered. Resultant solid was washed with hexane and allowed to dry in vacuo to give an orange crystalline solid (8.00 g, 91%); δH (300 MHz, CDCl3) 7.50 (1H, s, CH═C); 7.31 (1H, t, Ar), 7.20–7.11 (1H, m, Ar), 6.95–6.89 (1H, m, Ar), 3.80 (3H, s, OCH3).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. washResultant solid was washed with hexane
  4. customto dry in vacuo

Sources & evidence

ORD record
ord-db62cfdb86f04ed894b55713234b0141
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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