Sodium Hydroxide → HCID 15166262, compound

HRID 727906Notes

Reaction equation

HRID 727906 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.[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH2:22]Cl)[C:17]=1[CH3:24].[OH-].[Na+]>C(O)C>[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([CH2:22][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:17]=1[CH3:24]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19600555HCID 19600555, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 15166262HCID 15166262, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

12.3 g of crude 2-mercaptobenzimidazole, 20 g of 4-(2-chloroethoxy)-2-chloromethyl-3-methylpyridine hydrochloride and 11 g of sodium hydroxide were dissolved in 300 ml of ethanol to obtain a solution. This solution was stirred at 60° C. for 2 hours and distilled under a reduced pressure to remove the ethanol. The obtained residue was chromatographed over a silica gel column and eluted with 40% ethyl acetate in hexane and then with ethyl acetate to obtain 15.5 g of the title compound as a white solid.

Workup

  1. customto obtain a solution
  2. distillationdistilled under a reduced pressure
  3. customto remove the ethanol
  4. customThe obtained residue was chromatographed over a silica gel column
  5. washeluted with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1137b3cfc7b549369f7d97426b9981b0
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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