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Hydrochloric Acid → Ethyl 2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylate

HRID 2165933
Notes
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Reaction equation

HRID 2165933 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10]Br)=[C:6]([CH2:14][CH2:15][CH3:16])[C:5]=1[OH:17])(=[O:3])[CH3:2].[SH:18][C:19]1[NH:20][C:21]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][C:22]=2[N:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][S:18][C:19]2[NH:20][C:21]3[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][C:22]=3[N:23]=2)=[C:6]([CH2:14][CH2:15][CH3:16])[C:5]=1[OH:17])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 138819842-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethyl bromideHCID 178468678HCID 178468678, compound

Product 1

HCID 23042703Ethyl 2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylateYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethyl bromide (2.71 g), ethyl 2 mercaptobenzimidazole-5-carboxylate (2.00 g) and anhydrous potassium carbonate (1.49 g) in N,N-dimethylformamide (30 ml) was stirred at 80-90 ° C. for 30 minutes. The reaction 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 dichloro-methane-ethyl acetate (10:1), to give ethyl 2-[2-(4-acetyl-3- hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylate (2.33 g, 58.5 %) as a yellow oil.

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 dichloro-methane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-75f3bd55358249e88a52045c386d9fa0
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