Water → HCID 85585332, compound

HRID 2073516Notes

Reaction equation

HRID 2073516 reaction equation
S(O[CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)(C1C=CC(C)=CC=1)(=O)=O.[N-:29]=[N+:30]=[N-:31].[Na+].O>CS(C)=O>[N:29]([CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)=[N+:30]=[N-:31]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86743861HCID 86743861, compound

Product 1

HCID 85585332HCID 85585332, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-[4-(2-Tosyloxyethoxy)Benzyl]-2,4-Thiazolidinedione (12.5 g) in dry Dimethylsulphoxide (80 ml) was added sodium azide (2 g) in one portion. The mixture was stirred at ambient temperature for 18 hours and the resulting solution added to water (250 ml). The aqueous solution was extracted with dichloromethane (2×300 ml) and the combined organic phases were washed with water (3×300 ml), dried (MgSO4), filtered and evaporated to give the title compound as an oil which was used in the next stage without further purification.

Workup

  1. extractionThe aqueous solution was extracted with dichloromethane (2×300 ml)
  2. washthe combined organic phases were washed with water (3×300 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-63d5d0bc5d734407b63fa7c7c825c973
Source dataset
uspto-grants-1990_04
Patent number
US04918091

Reaction notes

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