Acetic Acid → 5-[4-(1-Benzylbenzimidazol-5-ylmethoxy)benzyl]thiazolidine-2,4-dione hemihydrate

HRID 1419101Notes

Reaction equation

HRID 1419101 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][O:18][C:19]3[CH:51]=[CH:50][C:22]([CH2:23][CH:24]4[S:28][C:27](=[O:29])[N:26](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C:25]4=[O:49])=[CH:21][CH:20]=3)=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(=O)([O-])O.[Na+]>O>[OH2:18].[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][O:18][C:19]3[CH:51]=[CH:50][C:22]([CH2:23][CH:24]4[S:28][C:27](=[O:29])[NH:26][C:25]4=[O:49])=[CH:21][CH:20]=3)=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][O:18][C:19]3[CH:51]=[CH:50][C:22]([CH2:23][CH:24]4[S:28][C:27](=[O:29])[NH:26][C:25]4=[O:49])=[CH:21][CH:20]=3)=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 867539805-[4-(1-Benzylbenzimidazol-5-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione

Product 1

HCID 882050585-[4-(1-Benzylbenzimidazol-5-ylmethoxy)benzyl]thiazolidine-2,4-dione hemihydrateYield 101.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 0.26 g of 5-[4-(1-benzylbenzimidazol-5-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 29), 3 ml of acetic acid and 1 ml of water was stirred for 3 hours at 50° C. in oil bath. At the end of this time, the reaction mixture was neutralized with sodium hydrogencarbonate and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was recrystallized from a mixture of ethanol and methanol, to give 116 mg of the title compound, melting at 185°-187° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was then removed by evaporation under reduced pressure
  5. customthe resulting residue was recrystallized from a mixture of ethanol and methanol

Sources & evidence

ORD record
ord-5a1c3862049a44319306ebc66244c3d2
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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