Sodium Hydroxide → 6-[[(5-methyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo(4,5-f)benzimidazole

HRID 1583775Notes

Reaction equation

HRID 1583775 reaction equation
[O:1]1[C:13]2[C:4](=[CH:5][C:6]3[NH:10][C:9]([SH:11])=[N:8][C:7]=3[CH:12]=2)[O:3][CH2:2]1.[OH-].[Na+].Cl.Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1>O>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][S:11][C:9]2[NH:10][C:6]3[CH:5]=[C:4]4[O:3][CH2:2][O:1][C:13]4=[CH:12][C:7]=3[N:8]=2)=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideHCID 178527753HCID 178527753, compound

Product 1

HCID 233137996-[[(5-methyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo(4,5-f)benzimidazoleYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9.8 g of 5H-1,3-dioxolo(4,5-f)-benzimidazole-6-thiol were suspended in 200 ml of alcohol in a 500 ml sulfonation flask equipped with stirrer, thermometer, dropping funnel and reflux condenser and treated dropwise while stirring well with a solution of 4.47 g of sodium hydroxide in 100 ml of water. The mixture was stirred at room temperature for an additional 30 minutes. Then 9.15 g of 2-chloromethyl-5-methylpyridine hydrochloride were added thereto. The mixture was left to boil at reflux overnight and subsequently evaporated. The residue was taken up in 500 ml of ethyl acetate, extracted with 100 ml of 3N sodium hydroxide and washed neutral with water. The aqueous extracts were extracted once more with 500 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated in vacuo. After recrystallization from acetonitrile, the residue gave 13.3 g (87.6% of theory) of 6-[[(5-methyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo(4,5-f)benzimidazole of melting point 187°-188° C. When the residue was dissolved with heating in 50 ml of methanol and treated with 100 ml of 5N hydrochloric acid in ethyl acetate, there were obtained, with the same yield, 16.5 g of dihydrochloride of melting point 232°-234° C.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. additiontreated dropwise
  4. waitThe mixture was left
  5. temperatureat reflux overnight
  6. customsubsequently evaporated
  7. extractionextracted with 100 ml of 3N sodium hydroxide
  8. washwashed neutral with water
  9. extractionThe aqueous extracts were extracted once more with 500 ml of ethyl acetate
  10. dry with materialThe combined organic phases were dried over sodium sulfate
  11. customevaporated in vacuo
  12. customAfter recrystallization from acetonitrile

Sources & evidence

ORD record
ord-1cfb749d9e04426a99a6903081bf5db6
Source dataset
uspto-grants-1985_11
Patent number
US04554280

Reaction notes

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