HCID 18404138, compound → HCID 19075193, compound

HRID 581741Notes

Reaction equation

HRID 581741 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

Conditions

Temperature
55 °C

Procedure

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

Workup

  1. distillationethanol is distilled off on a rotary evaporator (1 kPa/40° C.)
  2. extractionthe residue is extracted 3 times with 20 ml of dichloromethane each time
  3. washthe extracts are washed with 0.1 N sodium hydroxide solution
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated completely in vacuo
  6. customFor purification
  7. customthe crude product is chromatographed on silica gel (dichloromethane/methanol 20:1)
  8. concentrationthe collected pure fractions are jointly concentrated in vacuo
  9. customthe residue is crystallized from dichloromethane/diisopropyl ether
  10. customIt is then recrystallized from methanol/toluene

Sources & evidence

ORD record
ord-d1a015e557c44c3fbf8859577f865fc7
Source dataset
uspto-grants-1999_07
Patent number
US05922720

Reaction notes

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