Sodium Methoxide → HCID 178488125, compound

HRID 1067034Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

5-Methoxy-2-[(3,5-dimethyl-4-nitro-2-pyridinyl)methylthio]-1H-benzimidazole (IX) (50 gm, 0.145 mole) was dissolved in methanol and heated to 45° C. A solution of sodium methoxide (50 gm, 0.925 mole) in methanol (150 ml) was added dropwise over a period of 3 hours at 45-60° C. Stirring was continued for another 2 hours and then methanol was distilled off under reduced pressure. To the cooled residue was added water (200 ml) followed by concentrated HCl (65 ml) until the pH of the mixture was 7.5. The reaction mixture was extracted with dichloromethane and the dichloromethane layer was washed with water (2×100 ml). The dichloromethane layer was dried over sodium sulfate and concentrated to yield the product as an amber color syrup. Yield was 40.1 gm, about 83.8% of theoretical. A solid sample was obtained by trituration of the syrup several times with petroleum ether.

Workup

distillationmethanol was distilled off under reduced pressure
additionTo the cooled residue was added water (200 ml)
extractionThe reaction mixture was extracted with dichloromethane
washthe dichloromethane layer was washed with water (2×100 ml)
dry with materialThe dichloromethane layer was dried over sodium sulfate
concentrationconcentrated
customto yield the product as an amber color syrup

Sources & evidence

ORD record: ord-137cd3738b7a4fa6908e913db03e0229
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06245913B1

Reaction notes

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