HCID 85585332, compound → HCID 11551221, compound

HRID 2073515Notes

Reaction equation

HRID 2073515 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH2:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([CH2:11][CH:12]2[S:16][C:15](=[O:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 85585332HCID 85585332, compound

Product 1

HCID 11551221HCID 11551221, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-[4-(2-Azidoethoxy)Benzyl]2,4-Thiazolidinedione (5 g) in Methanol (100 ml) was reduced under hydrogen at ambient temperature and pressure in the presence of 10% palladium on charcoal (5 g) for 18 hours. The mixture was filtered through diatomaceous earth and the filter pad was washed exhaustively with Methanol. The combined filtrates was evaporated to dryness under reduced pressure and the title compound (m.p. 175°-6° C.) was obtained as a dihydrate following crystallisation from methanol.

Workup

  1. customwas reduced under hydrogen at ambient temperature
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washthe filter pad was washed exhaustively with Methanol
  4. customThe combined filtrates was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f397d873a105467088b3b77f059efa28
Source dataset
uspto-grants-1990_04
Patent number
US04918091

Reaction notes

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