Hydrazine hydrate (1:1) → 5-[4-(2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dione

HRID 1941666Notes

Reaction equation

HRID 1941666 reaction equation
O.NN.C1(=O)[N:8]([O:9][CH2:10][CH2:11][O:12][C:13]2[CH:26]=[CH:25][C:16]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:15][CH:14]=2)C(=O)C2=CC=CC=C12>C(O)C>[NH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH:18]2[S:22][C:21](=[O:23])[NH:20][C:19]2=[O:24])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21834037HCID 21834037, compound

Product 1

HCID 218339665-[4-(2-Aminooxyethoxy)benzyl]thiazolidine-2,4-dioneYield 106.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

0.32 ml of hydrazine monohydrate was added to a suspension of 2.64 g of 5-[4-(2-phthalimidooxyethoxy)-benzyl]thiazolidine-2,4-dione [prepared as described in step (d) above] in 30 ml of ethanol, and the resulting mixture was stirred at 80° C. for 2 hours. At the end of this time, the reaction mixture was cooled and the precipitated phthalhydrazide was filtered off. The filtrate was concentrated by evaporation under reduced pressure, and the concentrate was purified by column chromatography through silica gel, using a 1:20 by volume mixture of methanol and methylene chloride as the eluent, to give 1.93 g of 5-[4-(2-aminooxyethoxy)benzyl]-thiazolidine-2,4-dione as a syrup.

Workup

  1. temperatureAt the end of this time, the reaction mixture was cooled
  2. filtrationthe precipitated phthalhydrazide was filtered off
  3. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  4. customthe concentrate was purified by column chromatography through silica gel
  5. additionby volume mixture of methanol and methylene chloride as the eluent

Sources & evidence

ORD record
ord-274b5de2ca22458f836683e19a6ba2c4
Source dataset
uspto-grants-1997_12
Patent number
US05703096

Reaction notes

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