Sodium Acetate → 5-[[7-[(5-Ethyl-2-pyridinyl)methoxy]quinolin-3-yl]methyl]-2-imino-1,3-thiazolidin-4-one

HRID 1938346Notes

Reaction equation

HRID 1938346 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][N:21]=1)[CH:12]=2)[C:3]([O:5]C)=O.[NH2:28][C:29]([NH2:31])=[S:30].C([O-])(=O)C.[Na+]>C(O)C>[CH2:26]([C:23]1[CH:24]=[CH:25][C:20]([CH2:19][O:18][C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:8]([CH2:7][CH:2]4[S:30][C:29](=[NH:28])[NH:31][C:3]4=[O:5])[CH:9]=[N:10]3)=[CH:15][CH:14]=2)=[N:21][CH:22]=1)[CH3:27]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 21469288Methyl 2-bromo-3-[7-(5-ethyl-2-pyridylmethoxy)-3-quinolyl]propionate

Product 1

HCID 1415769645-[[7-[(5-Ethyl-2-pyridinyl)methoxy]quinolin-3-yl]methyl]-2-imino-1,3-thiazolidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (20 mL) was dissolved the crude residue (790 mg) of methyl 2-bromo-3-[7-(5-ethyl-2-pyridylmethoxy)-3-quinolyl]propionate. The solution was heated under reflux for 15 hours after addition of thiourea (140 mg, 1.84 mmol.) and sodium acetate (150 mg, 1.84 mmol.). After the completion of reaction was confirmed, ethanol was distilled off. To the residue were added ethyl acetate and aqueous sodium hydrogen carbonate. The organic portion was recovered, washed with water, and dried over sodium sulfate.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 15 hours
  3. customAfter the completion of reaction
  4. distillationethanol was distilled off
  5. additionTo the residue were added ethyl acetate and aqueous sodium hydrogen carbonate
  6. customThe organic portion was recovered
  7. washwashed with water
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-b4c2325227fb431a821ce6554d1a385d
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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