Ammonia → 5-Methoxy-2-(4-methyl-2-pyridylthiomethyl)benzimidazole

HRID 414189Notes

Reaction equation

HRID 414189 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH2:9][C:10](OCC)=O)[CH:3]=1.Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]([NH2:25])[CH:19]=1.N>Cl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]2[N:24]=[C:10]([CH2:9][S:8][C:4]3[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=3)[NH:25][C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 122529004-Methoxybenzene-1,2-diamine hydrochlorideHCID 21281961Ethyl 2-(4-methyl-2-pyridylthio)acetate

Product 1

HCID 212819535-Methoxy-2-(4-methyl-2-pyridylthiomethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

10.6 g of ethyl 2-(4-methyl-2-pyridylthio)acetate (0.05 mole) and 8.8 g of 4-methoxy-1,2-phenylenediamine hydrochloride (0.05 mole) in 400 ml of 6N hydrochloric acid are heated under reflux for 2 days. The mixture is allowed to cool and is neutralized with ammonia solution. It is extracted with ethyl acetate (3×100 ml), and the extract is dried (Na2SO4), filtered and concentrated to a volume of 75 ml. From this solution, 8.4 g (59%) of 5-methoxy-2-(4-methyl-2-pyridylthiomethyl)benzimidazole, melting point 138°-140° C., crystallize. The data for the identification of the product appear in Tables 1 and 2.

Workup

  1. temperatureunder reflux for 2 days
  2. temperatureto cool
  3. extractionIt is extracted with ethyl acetate (3×100 ml)
  4. dry with materialthe extract is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a volume of 75 ml
  7. customFrom this solution, 8.4 g (59%) of 5-methoxy-2-(4-methyl-2-pyridylthiomethyl)benzimidazole, melting point 138°-140° C., crystallize

Sources & evidence

ORD record
ord-e9dbed3d682d449db8c119668b2829df
Source dataset
uspto-grants-1988_12
Patent number
US04791114

Reaction notes

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