Hydrochloric Acid → HCID 827942, compound

HRID 2231251Notes

Reaction equation

HRID 2231251 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[C:7]3[C:12]([CH:13]=[CH:14][C:4]=2[N:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[H-].[Na+].[CH3:17]I.Cl>O1CCCC1.O>[CH3:1][C:2]1[N:3]([CH3:17])[C:4]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:5]=2[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178432073HCID 178432073, compound

Product 1

HCID 827942HCID 827942, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8.56 g of 2-methyl-1H-naphth[1,2-d]imidazole in 100 ml of tetrahydrofuran was added over a period of 15 minutes 2.25 g of 50% sodium hydride in oil and the mixture allowed to stir for 20 minutes. Methyl iodide (2.93 ml) was added over a 5-minute period and the reaction mixture allowed to stir at room temperature overnight. The reaction mixture was poured into water and the pH adjusted to 2 with 12N hydrochloric acid. The aqueous acid was extracted with chloroform (2×100 ml) and the pH adjusted to 10 with ammonium hydroxide. The aqueous base was extracted with chloroform (2×100 ml) and the combined extracts dried and concentrated to give 7.75 g of the isomers as a tan solid.

Workup

  1. stirringto stir at room temperature overnight
  2. extractionThe aqueous acid was extracted with chloroform (2×100 ml)
  3. extractionThe aqueous base was extracted with chloroform (2×100 ml)
  4. customthe combined extracts dried
  5. concentrationconcentrated
  6. customto give 7.75 g of the isomers as a tan solid

Sources & evidence

ORD record
ord-858bb33e7ad6402198eea27c154e36e6
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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