Ammonium Acetate → 4-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile

HRID 1297632Notes

Reaction equation

HRID 1297632 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:16]#[N:17])[CH3:2].[S:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[S:20].C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:24]3/[C:22](=[O:23])[NH:21][C:19](=[S:20])[S:18]/3)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:16]#[N:17])[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 1201546RhodanineHCID 58585818HCID 58585818, compound

Product 1

HCID 585857804-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The suspension of 4-ethoxy-6-formyl-quinoline-3-carbonitrile (example 14e, 1.13 g, 5 mmol) and rodahnine (2-thioxo-thiazolin-4-one) (1.0 g, 7.5 mmol) in anhydrous toluene (50 mL) was added ammonium acetate (0.77 g, 10 mmol). The mixture was stirred under reflux for 6 h. After cooling to room temperature, the solid was collected by filtration, washed with water, toluene and dried to obtain 4-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (1.7 g, 100%) as a grey solid. LC-MS m/e 342 (MH+)

Workup

  1. temperatureunder reflux for 6 h
  2. filtrationthe solid was collected by filtration
  3. washwashed with water, toluene
  4. customdried

Sources & evidence

ORD record
ord-5203bd926df14b09b6ce4faba2332ecd
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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