Sodium Hydroxide → HCID 19996498, compound

HRID 2248439Notes

Reaction equation

HRID 2248439 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([SH:11])[NH:7][C:6]=2[CH:5]=[C:4]([CH3:12])[C:3]=1[O:13][CH3:14].[OH-].[Na+].Cl.[CH3:18][C:19]1[C:20]([CH2:26]Cl)=[N:21][CH:22]=[CH:23][C:24]=1[CH3:25]>CO.O>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([S:11][CH2:26][C:20]3[C:19]([CH3:18])=[C:24]([CH3:25])[CH:23]=[CH:22][N:21]=3)[NH:7][C:6]=2[CH:5]=[C:4]([CH3:12])[C:3]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 199964993,4-Dimethyl-2-chloromethylpyridine hydrochlorideHCID 178489086HCID 178489086, compound

Product 1

HCID 19996498HCID 19996498, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To 4,6-dimethyl-5-methoxy-2-mercapto-1H-benzimidazole (1.04 g, 0.0050 mol) in methanol (50 ml) were added (in the following order) NaOH (0.2 g, 0.0050 mol) dissolved in water (2 ml) and 3,4-dimethyl-2-chloromethylpyridine hydrochloride (0.96 g, 0.0050 mol). The mixture was heated until reflux. NaOH (0.2 g, 0.0050 mol) dissolved in water (2 ml) was added dropwise and then the reflux was continued for 3 hours. The mixture was poured on ice-water (200 ml). Filtration and recrystallization from CH3CN gave the desired product (1.1 g, 67%). NMR data for the final product is given below.

Workup

  1. temperatureThe mixture was heated
  2. temperatureuntil reflux
  3. additionwas added dropwise
  4. additionThe mixture was poured on ice-water (200 ml)
  5. filtrationFiltration and recrystallization from CH3CN

Sources & evidence

ORD record
ord-c2f88b031b4a48d5ba58e4a47a9dae02
Source dataset
uspto-grants-1991_08
Patent number
US05039806

Reaction notes

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