Hydrochloric Acid → HCID 23362237, compound

HRID 1082114Notes

Reaction equation

HRID 1082114 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24]C(=O)N[C:21]2=[O:26])=[CH:17][CH:16]=1)[CH3:11].Cl.[OH-:30].[Na+]>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][CH:20]([SH:24])[C:21]([OH:26])=[O:30])=[CH:27][CH:28]=1)[CH3:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9822139HCID 9822139, compound

Product 1

HCID 23362237HCID 23362237, compound

Procedure

A solution of 5-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]benzyl]-2,4-thiazolidinedione (Eur. Patent Appl., Publication No. 0306228) (1.0 g) in 10% aqueous sodium hydroxide solution (25 mL) was heated at reflux under a nitrogen atmosphere for 1.75 hrs. The mixture was cooled, acidified to pH3 with concentrated hydrochloric acid and extracted with ethyl acetate (300 mL). The organic solution was washed with brine (100 mL), dried (MgSO4) and evaporated. The residue was redissolved in boiling ethyl acetate, filtered and allowed to cool and crystallise to afford the title compound, mp 154°-6° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 1.75 hrs
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl acetate (300 mL)
  4. washThe organic solution was washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was redissolved
  8. filtrationfiltered
  9. temperatureto cool
  10. customcrystallise

Sources & evidence

ORD record
ord-9eccb07c8f4a43aba55503eb8b7e1557
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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