Sodium Hydroxide → HCID 20142796, compound

HRID 649218Notes

Reaction equation

HRID 649218 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.[OH-].[Na+].Br[CH2:18][C:19]1[C:24]([O:25][CH3:26])=[C:23]([O:27][CH3:28])[CH:22]=[CH:21][N:20]=1>CO>[CH3:26][O:25][C:24]1[C:19]([CH2:18][S:10][C:8]2[NH:9][C:5]3[CH:4]=[C:3]([C:2]([F:13])([F:1])[F:14])[CH:12]=[CH:11][C:6]=3[N:7]=2)=[N:20][CH:21]=[CH:22][C:23]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 201428022-Bromomethyl-3,4-dimethoxypyridineHCID 178506086HCID 178506086, compound

Product 1

HCID 20142796HCID 20142796, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 5-trifluoromethyl-2-mercaptobenzimidazole (1.10 g), 1N-sodium hydroxide (7.2 ml), and methanol (5 ml) was added a solution of 2-bromomethyl-3,4-dimethoxypyridine (1.3 g) in methanol (35 ml) at room temperature over 10 minutes. The mixture was stirred for one hour, concentrated, and extracted with chloroform. The organic layer was washed with 1N-sodium hydroxide and then with water, dried, and evaporated. The residue was purified by column chromatography on silica gel (chloroform-ethyl acetate-acetone (1:1:0.1)) and recrestallized from chloroform-isopropyl ether, to give 2-[(3,4-dimethoxypyrid-2-yl)methylthio]-5-trifluoromethylbenzimidazole (310 mg) as white crystals.

Workup

  1. concentrationconcentrated
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with 1N-sodium hydroxide
  4. dry with materialwith water, dried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (chloroform-ethyl acetate-acetone (1:1:0.1))

Sources & evidence

ORD record
ord-8995c17d3a17428bb804ac0a145b551b
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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