Methyl iodide → 2-(methylthio)-1H-naphtho[2,3-d]imidazole

HRID 1413108Notes

Reaction equation

HRID 1413108 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:4]=2[N:3]=[C:2]1[SH:14])[CH:11]=[CH:10][CH:9]=[CH:8]3.[OH-].[Na+].[CH3:17]I>C(O)C.O>[CH3:17][S:14][C:2]1[NH:3][C:4]2[CH:13]=[C:12]3[C:7](=[CH:6][C:5]=2[N:1]=1)[CH:8]=[CH:9][CH:10]=[CH:11]3

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1785277551H-benzo[f]benzimidazole-2-thiol

Product 1

HCID 128720792-(methylthio)-1H-naphtho[2,3-d]imidazoleYield 122.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

20.0 g of 1H-naphth[2,3-d]imidazole-2-thiol and 4.0 g of sodium hydroxide were heated for 1 hour under reflux and in 150 ml of ethanol with 6.5 g of methyl iodide. The reaction solution was diluted with 500 ml of water and the precipitated product was suction filtered. Crystallisation from dioxane provided 12.0 g of 2-methylthio-1H-naphth[2,3-d]imidazole having a m.p. of 242°-244°.

Workup

  1. filtrationfiltered
  2. customCrystallisation from dioxane

Sources & evidence

ORD record
ord-ed7c4aa2069d4b7abeca585c00ebd11f
Source dataset
uspto-grants-1981_02
Patent number
US04248880

Reaction notes

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