Hydrochloric Acid → Rivoglitazone hydrochloride

HRID 413775Notes

Reaction equation

HRID 413775 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][O:12][C:13]3[CH:26]=[CH:25][C:16]([CH2:17][CH:18]4[S:22][C:21](=[O:23])[NH:20][C:19]4=[O:24])=[CH:15][CH:14]=3)[N:8]([CH3:27])[C:7]=2[CH:28]=1.[ClH:29]>O1CCOCC1>[ClH:29].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:17][CH:18]4[S:22][C:21](=[O:23])[NH:20][C:19]4=[O:24])=[CH:25][CH:26]=3)[N:8]([CH3:27])[C:7]=2[CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3055168Rivoglitazone

Product 1

HCID 9889104Rivoglitazone hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-[4-(6-methoxy-1-methyl-1H-benzimidazol-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (10.6 g) and 4N hydrochloric acid in 1,4-dioxane (100 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated, and to the residue was added ethyl acetate to form a precipitate. The precipitate was collected by filtration and washed with ethyl acetate to afford the title compound (11.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionto the residue was added ethyl acetate
  3. customto form a precipitate
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7a203dc9536248c78ab9bae723c0f767
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

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