Potassium Carbonate → HCID 20142793, compound

HRID 649217Notes

Reaction equation

HRID 649217 reaction equation
[K].[SH:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[C:25]([O:26][CH3:27])=[C:24]([O:28][CH2:29][CH3:30])[CH:23]=[CH:22][N:21]=1>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:29]([O:28][C:24]1[CH:23]=[CH:22][N:21]=[C:20]([CH2:19][S:2][C:3]2[NH:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[C:25]=1[O:26][CH3:27])[CH3:30]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5462222PotassiumHCID 20142798HCID 20142798, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 20142793HCID 20142793, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of potassium salt of 2-mercaptobenzimidazole (1.3 g) and potassium carbonate (1.0 g) in dimethylformamide (15 ml) was added with stirring, a solution of 2-bromomethyl-4-ethoxy-3-methoxy-pyridine (1.6 g) in dimethylformamide (5 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with chloroform (50 ml), washed with water, 1N-sodium hydroxide, and water in this order, dried, and evaporated. The residue was purified by column chromatography on silica gel (chloroform-methanol (50:1)), to give 2-[(4-ethoxy-3-methoxypyrid-2-yl)methylthio]benzimidazole (1.4 g) as a light yellow oil.

Workup

  1. additionwas added
  2. washwashed with water, 1N-sodium hydroxide, and water in this order
  3. customdried
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel (chloroform-methanol (50:1))

Sources & evidence

ORD record
ord-e11a0ece7be14e39a223a2426426e570
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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