Sodium Hydroxide → HCID 19962997, compound

HRID 1720059Notes

Reaction equation

[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][N:12]([CH3:30])[CH:13]([CH2:19][S:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH2:27]Cl)[C:22]=1[CH3:29])[C:14]([O:16][CH2:17][CH3:18])=[O:15].[OH-].[Na+]>C(O)C>[CH3:29][C:22]1[C:23]([CH2:27][S:1][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)=[N:24][CH:25]=[CH:26][C:21]=1[S:20][CH2:19][CH:13]([N:12]([CH3:30])[CH3:11])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

2-Mercaptobenzimidazole (1.5 g) was dissolved in ethanol (20 ml) and thereto were added ethyl 2-dimethylamino-3-(2-chloromethyl-3-methyl-4-pyridylthio)propionate (3.16 g) and an aqueous solution (10 ml) of 1N sodium hydroxide. The mixture was stirred at 50° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled away under reduced pressure. The residue was subjected to column chromatography and eluted with chloroform-methanol to give 2-((3-methyl-4-(2-dimethylamino-2-ethoxycarbonylethylthio)-2-pyridyl)methylthio)-1H-benzimidazole as a pale yellow oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure and water
additionwas added to the residue
extractionThe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled away under reduced pressure
washeluted with chloroform-methanol

Sources & evidence

ORD record: ord-a1502d939e484401940d3c1384dc3bc6
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05504082

Reaction notes

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