Potassium Carbonate → HCID 17836482, compound

HRID 348511Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=3[N:13]=[C:12]2[SH:22])=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35]Br)[CH3:30]>CN(C)C=O>[CH2:29]([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35][S:22][C:12]1[N:11]([CH2:10][C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][CH:2]=2)[C:15]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=2[N:13]=1)[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

101 mg (0.30 mmol) of 1-((benzothiophene-3-yl)methyl)-5-methoxybenzimidazole-2-thiol were dissolved in 2 ml of dimethylformamide followed by the addition of 62 mg (0.45 mmol) of potassium carbonate and 53 mg (0.40 mmol) of 4-bromobutanoate ethyl ester and heating to 80° C. After 12 hours, the reaction solution was concentrated under reduced pressure and extracted with diethyl ether followed by washing twice with 10 ml of saturated brine and drying with magnesium sulfate. The solvent was then concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 60 mg (0.136 mmol) of 4-(1-((benzothiophene-3-yl)methyl)-5-methoxybenzimidazole-2-ylthio)butanoate ethyl ester (yield: 45%).

Workup

concentrationthe reaction solution was concentrated under reduced pressure
extractionextracted with diethyl ether
washby washing twice with 10 ml of saturated brine
dry with materialdrying with magnesium sulfate
concentrationThe solvent was then concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-432d52eeea7d418d96031e663999999d
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176320B2

Reaction notes

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