Potassium Carbonate → HCID 22903562, compound

HRID 1953133Notes

Reaction equation

HRID 1953133 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.Br[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]=1[S:1][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:13]#[N:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23303000HCID 23303000, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 22903562HCID 22903562, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-mercaptobenzimidazole (0.30 g, 3.0 mmole), bromo(2-pyridyl)acetonitrile (0.59 g, 3.0 mmole) and potassium carbonate (0.37 g 3.0 mmole) in 50 ml of dry N,N-dimethylformamide was heated at 60° C. for 6 h. The solvent was evaporated. The residue was dissolved in ethyl acetate, washed with water and then saturated sodium chloride solution. The organic layer was dried over magnesium sulfate and evaporated to give a solid. The crude product was further purified by column chromatography on silica gel (100% ethyl acetate) to give 66 mg (10%) of the title compound as a solid; mp 166-167° C.; 1H NMR (DMSO-d6)δ 9.3 (m, 1H), 8.65 (m, 2H), 8.32 (m, 1H), 7.78 (br s, 4H), 4.81 (br s, 2H) ppm; IR ν 2206, 1512, 1465, 1432, 1357, 1179, 740 cm-1.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customto give a solid
  7. customThe crude product was further purified by column chromatography on silica gel (100% ethyl acetate)

Sources & evidence

ORD record
ord-155f979056854f6bb13a8603d06be209
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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