Hydrochloric Acid → HCID 21286284, compound

HRID 2231245Notes

Reaction equation

HRID 2231245 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=2[N+:6]=1[O-:7].[H-].[Na+].[CH3:14]I.Cl>O.CN(C)C=O>[CH3:14][O:7][N:6]1[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=[C:2]1[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178433618HCID 178433618, compound

Product 1

HCID 21286284HCID 21286284, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7.8 g (0.53 mole) of 2-methylbenzimidazole N-oxide [Chem. Pharm. Bull., 11, 1375 (1963)]in 50 ml of dimethylformamide was added 2.53 g (0.053 mole) of 50% sodium hydride in oil over a period of 5 minutes. After stirring 15 minutes, 3.33 ml (0.053 mole) of methyl iodide was added over a 15-minute period and the reaction mixture allowed to stir at room temperature for 3 hours. The reaction was poured into water, the pH adjusted to 2 with 12N hydrochloric acid and the impurities extracted with ethyl acetate. The pH was adjusted to 12 with 6N sodium hydroxide solution and the product extracted with ethyl acetate (3×100 ml). The extracts were combined, dried over magnesium sulfate and evaporated under a nitrogen stream.

Workup

  1. stirringto stir at room temperature for 3 hours
  2. extractionthe impurities extracted with ethyl acetate
  3. extractionthe product extracted with ethyl acetate (3×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under a nitrogen stream

Sources & evidence

ORD record
ord-4f98960b5f494da299cb753fa27203d7
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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