Water → 5-[1-Quinolin-6-yl-meth-(z)-ylidene]-2-thioxo-thiazolidin-4-one

HRID 2053293Notes

Reaction equation

HRID 2053293 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[S:13]1[CH2:19][C:17](=[O:18])[NH:16][C:14]1=[S:15].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][C:7](/[CH:11]=[C:19]3/[C:17](=[O:18])[NH:16][C:14](=[S:15])[S:13]/3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 7656536-QuinolinecarbaldehydeHCID 1201546Rhodanine

Product 1

HCID 116662315-[1-Quinolin-6-yl-meth-(z)-ylidene]-2-thioxo-thiazolidin-4-oneYield 98.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The suspension of 6-quinolinecarboxaldehyde (6 g, 38 mmol), rhodanine (2-thioxo-4-thiazolidinone) (5.08 g, 38 mmol) and sodium acetate (12.5 g, 152 mmol) in acetic acid (50 mL) was stirred under reflux for 12 h. After cooling to room temperature, water (150 mL) was added. The solid was collected by filtration, washed with water and dried to obtain 5-[1-quinolin-6-yl-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one (10.2 g, 98%) as a yellow solid. LC-MS m/e 273 (MH+).

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-3a4b81b674b4453596f9dfe9689025bd
Source dataset
uspto-grants-2008_02
Patent number
US07326786B2

Reaction notes

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