Water → HCID 10000213, compound

HRID 2119924Notes

Reaction equation

HRID 2119924 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1.O.C(=O)(O)[O-].[Na+].[C:31](OC(=O)C)(=[O:33])[CH3:32]>O1CCOCC1>[C:31]([N:7]([CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1)[C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1)(=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 11725052HCID 11725052, compound

Product 1

HCID 10000213HCID 10000213, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 5-[4-(2-(2-pyrimidinylamino)ethoxy)benzyl]-2,4-thiazolidinedione (800 mg) in acetic anhydride (15 ml) and 1,4-dioxan (5 ml) was boiled under reflux for 3 hours. After cooling, the mixture was added to water (300 ml), neutralized (sodium bicarbonate) and extracted with dichloromethane (3×200 ml). The organic extracts were washed with brine (100 ml), dried (MgSO4), filtered and evaporated to dryness. Chromatography on silica-gel in dichloromethane of the residual oil afforded the title compound (m.p. 137° C.).

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane (3×200 ml)
  4. washThe organic extracts were washed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c6fe162fc05b41a7a5d78b6a1ddbfd09
Source dataset
uspto-grants-2004_02
Patent number
US06686475B2

Reaction notes

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