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

HRID 853018Notes

Reaction equation

HRID 853018 reaction equation
C(O[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[N:7]=[CH:6][CH:5]=1)C.[S:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[S:18].O>C(O)(=O)C>[N:7]1[C:8]2[C:13](=[CH:12][C:11](/[CH:14]=[C:22]3/[C:20](=[O:21])[NH:19][C:17](=[S:18])[S:16]/3)=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1201546RhodanineHCID 586153616-Quinolinecarboxaldehyde, 4-ethoxy-

Product 1

HCID 116662315-[1-Quinolin-6-yl-meth-(z)-ylidene]-2-thioxo-thiazolidin-4-oneYield 115.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The suspension of 4-ethoxy-quinoline-6-carbaldehyde (example 3b) (4.0 g, 20 mmol) and rhodanine (2.65 g, 20 mmol) in acetic acid (40 mL) was stirred under reflux for 12 h. After cooling to room temperature, water (50 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 (6.3 g, 100%) as a brown solid. LC-MS m/e 317 (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-2edf450a61124f1db998ff09ca44f174
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

Loading…