Sodium Acetate → 5-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

HRID 1380539Notes

Reaction equation

HRID 1380539 reaction equation
C([O:4][CH:5]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH3:28])=[CH:23][N:22]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15](Br)[C:16]([O:18]C)=O)=[CH:10][CH:9]=1)(=O)C.[NH2:29][C:30](N)=[S:31].C([O-])(=[O:35])C.[Na+]>C(O)C>[CH2:27]([C:24]1[CH:25]=[CH:26][C:21]([CH:5]([OH:4])[CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH:15]3[S:31][C:30](=[O:35])[NH:29][C:16]3=[O:18])=[CH:12][CH:13]=2)=[N:22][CH:23]=1)[CH3:28]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 14546507HCID 14546507, compound

Product 1

HCID 98642685-(4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzyl)thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

By following the same procedure as described in Example 1, methyl 3-{4-[2-acetoxy-2-(5-ethyl-2-pyridyl) ethoxy]phenyl}-2-bromopropionate (10.0 g), thiourea (2.0 g) and sodium acetate (2.2 g) were allowed to undergo reaction in ethanol and hydrolysis was performed to give 5-{4-[2-(5-ethyl-2-pyridyl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione in the form of crystals. Yield of 6.2 g. Recrystallization from ethyl acetate-hexane produced colorless prisms. m.p. 129°-130° C.

Workup

  1. customhydrolysis

Sources & evidence

ORD record
ord-fb87f50b3eb14a378ffa9e8029d2fb49
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

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