HCID 18404138, compound → HCID 19075193, compound

HRID 965007Notes

Reaction equation

HRID 965007 reaction equation
Cl.Cl[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])[CH:7]=[CH:6][N:5]=1.[SH:16][C:17]1[NH:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]=1>C(O)C.[OH-].[Na+]>[Cl:15][CH2:14][CH2:13][CH2:12][S:11][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:3][S:16][C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)[C:9]=1[CH3:10]

Participants

5

Reactant 2

HCID 18404138HCID 18404138, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 19075193HCID 19075193, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

One equivalent of 2-chloromethyl-4-(3-chloropropylthio)-3-methylpyridine hydrochloride (dissolved in 10 ml of water) is added dropwise to a solution of 2-mercapto-1H-benzimidazole (1.5 g/10 mmol) in 40 ml of ethanol and 21 ml of 1N sodium hydroxide solution at 40° C. in the course of 20 min. The mixture is then stirred at 50°-60° C. for 2-3 hours and at room temperature for a further 3-4 hours, the ethanol is distilled off on a rotary evaporator (1 kPa/40° C.), the residue is extracted 3 times with 20 ml of methylene chloride each time and the extract is washed with 0.1N sodium hydroxide solution, dried over potassium carbonate and evaporated to dryness in vacuo. For purification, the crude product is chromatographed over silica gel (methylene chloride 20:1 to 3:1); the pure fractions collected are evaporated together in vacuo and the residue is crystallized from methylene chloride/diisopropyl ether. It is then recrystallized from methanol/toluene. Yield: 2.67 g (74%) of the title compound as a colorless solid of melting point 112°-114° C.

Workup

  1. distillationthe ethanol is distilled off on a rotary evaporator (1 kPa/40° C.)
  2. extractionthe residue is extracted 3 times with 20 ml of methylene chloride each time
  3. washthe extract is washed with 0.1N sodium hydroxide solution
  4. dry with materialdried over potassium carbonate
  5. customevaporated to dryness in vacuo
  6. customFor purification
  7. customthe crude product is chromatographed over silica gel (methylene chloride 20:1 to 3:1)
  8. customthe pure fractions collected
  9. customare evaporated together in vacuo
  10. customthe residue is crystallized from methylene chloride/diisopropyl ether
  11. customIt is then recrystallized from methanol/toluene

Sources & evidence

ORD record
ord-42bbb288a6384d6c9670298dc2babc3d
Source dataset
uspto-grants-1998_06
Patent number
US05773451

Reaction notes

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