Imidazole → HCID 86754227, compound

HRID 581905Notes

Reaction equation

HRID 581905 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O.CO>[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N:21]4[CH:25]=[CH:24][N:23]=[CH:22]4)[CH:13]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 54320977HCID 54320977, compound

Product 1

HCID 86754227HCID 86754227, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1-(3-bromophenyl)-5-formylbenzimidazol O-methyloxime (29a) from Example 8 (0.7 g, 2.13 mmol), imidazole (0.33 g, 4.85 mmol), potassium carbonate (0.29 g, 2.13 mmol) and a catalytic amount of copper-bronze in 5 ml N-methyl-2-pyrrolidone is heated to 140° C. under a stream of nitrogen for 24 hours. After cooling the mixture is poured into water. A small volume of methanol is added and the mixture is extracted with dichloromethane. The extract is dried over sodium sulfate and concentrated under reduced pressure. The residue is eluted through silica gel with a mixture of dichloromethane and ethanol (10:1) to yield pure 29b. Yield: 0.23 g (34%) Mp. 197-199° C.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialThe extract is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue is eluted through silica gel with a mixture of dichloromethane and ethanol (10:1)

Sources & evidence

ORD record
ord-9352a411d2df438d8ad6017374fd421f
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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