3,4-Ethylendioxy-2-chloromethyl pyridine hydrochloride → 5-Acetyl-6-methyl-2-[[(3,4-ethylendioxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

HRID 1647157Notes

Reaction equation

HRID 1647157 reaction equation
[C:1]([C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[NH:8][C:9]([SH:11])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].Cl.[CH2:16]1[CH2:25][O:24][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([CH2:26]Cl)[C:18]=2[O:17]1>CO>[C:1]([C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[NH:8][C:9]([S:11][CH2:26][C:19]3[C:18]4[O:17][CH2:16][CH2:25][O:24][C:23]=4[CH:22]=[CH:21][N:20]=3)=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 199264673,4-Ethylendioxy-2-chloromethyl pyridine hydrochlorideHCID 178465846HCID 178465846, compound

Product 1

HCID 199264785-Acetyl-6-methyl-2-[[(3,4-ethylendioxy-2-pyridinyl)methyl]thio]-1H-benzimidazoleYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-acetyl-6-methyl-2-mercapto-1H-benzimidazole (0.14 g, 0.66 mmol) in methanol (2 ml) aqueous NaOH (0.25 ml 5M, 1.25 mmol) and 3,4-ethylendioxy-2-chloromethyl pyridine hydrochloride (0.13 g, 0.60 mmol) dissolved in methanol (2 ml) were added in the given order. The mixture was refluxed for one hour whereupon the solution was evaporated. The residue was partitioned between methylene chloride and water. After separation the organic solution was dried over Na2SO4 and evaporated giving a yellow syrup (0.17 g, 81%).

Workup

  1. additionwere added in the given order
  2. temperatureThe mixture was refluxed for one hour whereupon the solution
  3. customwas evaporated
  4. customThe residue was partitioned between methylene chloride and water
  5. customAfter separation the organic solution
  6. dry with materialwas dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-c161501b4146477ead15e7ae679d2c7d
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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