Hydrochloric Acid → Efatutazone Dihydrochloride

HRID 412378Notes

Reaction equation

HRID 412378 reaction equation
[NH2:1][C:2]1[C:34]([CH3:35])=[CH:33][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[C:13]([CH2:15][O:16][C:17]4[CH:30]=[CH:29][C:20]([CH2:21][CH:22]5[S:26][C:25](=[O:27])[NH:24][C:23]5=[O:28])=[CH:19][CH:18]=4)[N:12]([CH3:31])[C:11]=3[CH:32]=2)=[CH:4][C:3]=1[CH3:36].[ClH:37]>C(OCC)(=O)C>[ClH:37].[ClH:37].[NH2:1][C:2]1[C:3]([CH3:36])=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[C:13]([CH2:15][O:16][C:17]4[CH:18]=[CH:19][C:20]([CH2:21][CH:22]5[S:26][C:25](=[O:27])[NH:24][C:23]5=[O:28])=[CH:29][CH:30]=4)[N:12]([CH3:31])[C:11]=3[CH:32]=2)=[CH:33][C:34]=1[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9832447Efatutazone

Product 1

HCID 16719220Efatutazone Dihydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-[4-[6-(4-amino-3 ,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.25 g) and 4N hydrogen chloride in ethyl acetate (50 ml) was stirred at room temperature for 24 hours. The insoluble product was filtered and washed with ethyl acetate to afford the desired product (0.25 g, mp 165-175° C.).

Workup

  1. filtrationThe insoluble product was filtered
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0e166729d02b4a6daea007ac4e710f15
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

Loading…