Sodium Acetate → 5-(3-Methanesulfonyl-4-phenyl-quinolin-6-ylmethylene)-2-thioxo-thiazolidin-4-one

HRID 1297702Notes

Reaction equation

HRID 1297702 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([CH:21]=O)=[CH:10][CH:9]=2)(=[O:4])=[O:3].[S:23]1[CH2:29][C:27](=[O:28])[NH:26][C:24]1=[S:25].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([CH:21]=[C:29]1[S:23][C:24](=[S:25])[NH:26][C:27]1=[O:28])=[CH:10][CH:9]=2)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 1201546RhodanineHCID 585858373-Methanesulfonyl-4-phenyl-quinoline-6-carbaldehyde

Product 1

HCID 768238465-(3-Methanesulfonyl-4-phenyl-quinolin-6-ylmethylene)-2-thioxo-thiazolidin-4-oneYield 76.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-methanesulfonyl-4-phenyl-quinoline-6-carbaldehyde (example 611,78 mg, 0.25 mmol), rhodanine (67 mg, 0.50 mmol), sodium acetate (82 mg, 1.0 mmol), and acetic acid (2.5 mL) was heated under the microwave irradiation at 160 degrees for 40 min. After cooling to about room temperature, the reaction mixture was filtered, and the solid was collected, washed with water, dried to give 5-(3-methanesulfonyl-4-phenyl-quinolin-6-ylmethylene)-2-thioxo-thiazolidin-4-one (82 mg, 76%) with a yellow color. LC-MS m/e 427 (MH+).

Workup

  1. temperaturewas heated under the microwave irradiation at 160 degrees for 40 min
  2. temperatureAfter cooling to about room temperature
  3. filtrationthe reaction mixture was filtered
  4. customthe solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0a798ef00a264656bf2249411b0a0edf
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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