Hydrochloric Acid → HCID 12833668, compound

HRID 484655Notes

Reaction equation

HRID 484655 reaction equation
I.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][NH:16][C:17]([S:22][CH3:23])=[N:18][CH2:19][CH2:20][CH3:21])OCCO2)=[CH:6][CH:5]=1.[ClH:24].C(=O)([O-])O.[Na+]>>[ClH:24].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:18]([CH2:19][CH2:20][CH3:21])[C:17]([S:22][CH3:23])=[N:16][CH:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178457533HCID 178457533, compound

Product 1

HCID 12833668HCID 12833668, compoundYield 86%

Procedure

A mixture of 7 parts of methyl N-[2-(4-methoxyphenyl)-1,3-dioxolan-2-ylmethyl]-N'-propylcarbamimidothioate monohydroiodide and 30 parts of hydrochloric acid solution 10% is stirred and refluxed for 1.50 hours. The reaction mixture is cooled and neutralized with sodium hydrogen carbonate. The product is extracted with 1,1'-oxybisethane. The extract is dried, filtered and saturated with hydrogen chloride. The precipitated oil solidifies upon scratching. The product is filtered off and crystallized from a mixture of 2-propanol and 2,2'-oxybispropane, yielding 4 parts (86%) of 5-(4-methoxyphenyl)-2-(methylthio)-1-propyl-1H-imidazole monohydrochloride; mp. 149.2° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionThe product is extracted with 1,1'-oxybisethane
  4. customThe extract is dried
  5. filtrationfiltered and saturated with hydrogen chloride
  6. filtrationThe product is filtered off
  7. customcrystallized from a mixture of 2-propanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-9253c00a91f14afb92aedf951277ba11
Source dataset
uspto-grants-1985_08
Patent number
US04533550

Reaction notes

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