Sodium Hydroxide → 3-[(2-{[(1H-Benzimidazol-2-yl)sulfanyl]methyl}-3-methylpyridin-4-yl)oxy]propan-1-ol

HRID 357560Notes

Reaction equation

HRID 357560 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[CH2:12][C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:16]=[CH:15][N:14]=1.[OH-].[Na+]>C(O)C>[OH:24][CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S:1][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)[C:18]=1[CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 196005443-[[2-(Chloromethyl)-3-methyl-4-pyridinyl]oxy]-1-propanolHCID 178527775HCID 178527775, compound

Product 1

HCID 151662603-[(2-{[(1H-Benzimidazol-2-yl)sulfanyl]methyl}-3-methylpyridin-4-yl)oxy]propan-1-olYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

80 ml of ethanol was added to a mixture comprising 1.39 g (9.27 mmol) of 2-mercaptobenzimidazole, 2.0 g (9.27 mmol) of 2-chloromethyl-4-(3-hydroxypropoxy)-3-methylpyridine and 0.44 g (11.1 mmol) of sodium hydroxide. The obtained mixture was stirred at 50° C. for one hour. After the completion of the reaction, the reaction mixture was concentrated. The obtained residue was purified by silica gel column chromatography to obtain 1.7 g of the title compound (56%).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8d809ff70684faf9efe259c6944e30d
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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