Sodium Hydroxide → 5-Acetyl-6-methyl-2-[[(3,4-methylenedioxy-2pyridinyl)methyl]thio]-1H-benzimidazole
Reaction equation
Cl[CH2:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[CH:5][N:4]=1.[C:12]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[N:19]=[C:20]([SH:22])[NH:21][C:17]=2[CH:16]=1)(=[O:14])[CH3:13].[OH-].[Na+]>C(O)C.C(Cl)Cl.[Cl-].[Na+].O>[C:12]([C:15]1[C:24]([CH3:25])=[CH:23][C:18]2[NH:19][C:20]([S:22][CH2:2][C:3]3[C:8]4[O:9][CH2:10][O:11][C:7]=4[CH:6]=[CH:5][N:4]=3)=[N:21][C:17]=2[CH:16]=1)(=[O:14])[CH3:13]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
2-Chloromethyl-3,4-methylenedioxypyridine (90 mg, 0.52 mmol) and 5-acetyl-6-methyl-2-mercaptobenzimidazole (214 mg, 1.04 mmol) were dissolved in ethanol (15 ml). The pH value of the solution was adjusted to 9 (0.2M NaOH) whereupon the solution was refluxed for 10 min. After concentration of the reaction mixture at reduced pressure the residue was taken up in methylene chloride (10 ml) and brine (2 ml). The phases were separated and the organic phase was dried over sodium sulphate, filtered and concentrated at reduced pressure. The residue was chromatographed on silica (ethyl acetate). Yield: 140 mg (79%) of the title compound. Mp: 141°-143° C. (uncorr.)
Workup
- temperaturewas refluxed for 10 min
- customThe phases were separated
- dry with materialthe organic phase was dried over sodium sulphate
- filtrationfiltered
- concentrationconcentrated at reduced pressure
- customThe residue was chromatographed on silica (ethyl acetate)
Sources & evidence
- ORD record
- ord-8a361969308a47fbb89b1106ebf28252
- Source dataset
- uspto-grants-1995_07
- Patent number
- US05430042
Reaction notes
Loading…