Methanol → HCID 19858144, compound

HRID 2073245Notes

Reaction equation

HRID 2073245 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][N:13]2[C:17]3[CH:18]=[CH:19][C:20]([C:22]([OH:24])=[O:23])=[CH:21][C:16]=3[N:15]=[C:14]2[CH3:25])=[O:11])=[CH:8][C:7]=1[S:28](=[O:31])(=[O:30])[NH2:29].[CH3:32]O>>[Cl:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][N:13]2[C:17]3[CH:18]=[CH:19][C:20]([C:22]([O:24][CH3:32])=[O:23])=[CH:21][C:16]=3[N:15]=[C:14]2[CH3:25])=[O:11])=[CH:8][C:7]=1[S:28](=[O:31])(=[O:30])[NH2:29]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 19858105HCID 19858105, compound

Product 1

HCID 19858144HCID 19858144, compoundYield 75%

Procedure

After dropping 1.46 ml of thionyl chloride to a solution containing 8.2 g of 1-(4'-chloro-3'-sulfamoylbenzoyl)amino-2-methyl-5-carboxybenzimidazole in 50 ml of methanol while stirring, the reaction mixture was refluxed for 5 hours. The clear solution obtained was evaporated to dryness under reduced pressure and the solid residue was triturated with 1N sodium bicarbonate solution. After decanting the solution from the solid product, the residue was recrystallized from a mixture of dioxane and water (1:1). Thus, 6.35 g (75%) of 1-(4'-chloro-3'-sulfamoylbenzoyl)amino-5-methoxycarbonyl-2-methylbenzimidazole were obtained, m.p.: 251°-252° C. (with decomposition).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. customThe clear solution obtained
  3. customwas evaporated to dryness under reduced pressure
  4. customthe solid residue was triturated with 1N sodium bicarbonate solution
  5. customAfter decanting the solution from the solid product
  6. customthe residue was recrystallized from a mixture of dioxane and water (1:1)

Sources & evidence

ORD record
ord-0ea08046be3d44c88b6977cd4675971a
Source dataset
uspto-grants-1990_04
Patent number
US04916149

Reaction notes

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