Water → HCID 178423500, compound

HRID 1696622Notes

Reaction equation

HRID 1696622 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.Br[C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][C:13]3[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=3)=[N:3][C:4]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 784285-Bromothiophene-2-carbaldehydeHCID 178423448HCID 178423448, compound

Product 1

HCID 178423500HCID 178423500, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

a mixture of 0.82 g of 2-mercapto-5-methyl-benzimidazole (5 mmoles), 0.6 ml of 5-bromo-2-thiophenecarboxaldehyde (5 mmoles) and 1.4 g of potassium carbonate in 10 ml of DMF is heated at 110° C. for 2 hours. The mixture is cooled down to room temperature, then poured into 200 ml of water and extracted twice with 50 ml of ethyl acetate. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated. The crude product is purified on silica gel using DCM/MeOH as eluent to give 0.65 g of 5-(5-methyl-1H-benzimidazol-2-ylsulfanyl)-thiophene-2-carbaldehyde. (Yield=47%). Analytical LC/MS method A: ([M+H]+): 275). RT: 3.42 min (gradient 5 to 85% acetonitrile in 7 min).

Workup

  1. temperatureThe mixture is cooled down to room temperature
  2. extractionextracted twice with 50 ml of ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product is purified on silica gel

Sources & evidence

ORD record
ord-85642050dc3845aab278fc1abdbccce5
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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