Sodium Acetate → HCID 145821477, compound

HRID 1756638Notes

Reaction equation

HRID 1756638 reaction equation
Br[CH:2]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][N:18]=2)=[CH:10][CH:9]=1)[C:3]([O:5]C)=O.[NH2:26][C:27]([NH2:29])=[S:28].C([O-])(=O)C.[Na+]>C(O)C>[C:24]([CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH:2]3[S:28][C:27](=[NH:26])[NH:29][C:3]3=[O:5])=[CH:9][CH:10]=2)=[N:18][CH:19]=1)#[N:25]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 10525199HCID 10525199, compound

Product 1

HCID 145821477HCID 145821477, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 2-bromo-3-[4-[2-(5-cyanomethyl-2-pyridyl)ethoxy]phenyl]propionate (7.2 g), thiourea (1.2 g), sodium acetate (1.3 g) and ethanol (80 ml) was heated under reflux for 5 hours and concentrated under reduced pressure. To the residue was added saturated aqueous sodium bicarbonate solution (100 ml)-ether (50 ml) and the mixture was stirred for 15 minutes. The precipitated crystals were filtered off to obtain 5-[4-[2-(5-cyanomethyl-2-pyridyl)ethoxy]benzyl]-2-imino-4-thiazolidinone (2.5 g, yield: 38%). This compound was recrystallized from chloroform-methanol to obtain colorless prisms, m.p. 211°-212° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added saturated aqueous sodium bicarbonate solution (100 ml)-ether (50 ml)
  5. filtrationThe precipitated crystals were filtered off

Sources & evidence

ORD record
ord-cd1184c04af146029a4c2f567d99e409
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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