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Hydrochloric Acid → 2-[4-(4-Acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylic acid

HRID 2165941
Notes
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Reaction equation

HRID 2165941 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[C:23]([C:25]([O:27]CC)=[O:26])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2].O1CCOCC1.[OH-].[Na+].Cl>O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[CH:21][C:19]=3[N:20]=2)=[C:6]([CH2:30][CH2:31][CH3:32])[C:5]=1[OH:33])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 23042700Ethyl 2-[4-(4-acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylate

Product 1

HCID 146280732-[4-(4-Acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylic acidYield 64.5%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 2-[4-(4-acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylate (2.50 g), 1,4-dioxane (30 ml) and sodium hydroxide (1.03 g) in water (30 ml) was stirred at 60 ° C. for 2 hours. This mixture was poured into ice-water, made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-methanol (10:1), to give the title compound (1.52 g, 64.5 %) as yellow crystals, mp 90-95° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography
  6. washeluting with dichloromethane-methanol (10:1)

Sources & evidence

ORD record
ord-9ee0480b8dd148b2a130feb0005107be
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04942245

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes