Imidazole → HCID 10013146, compound

HRID 1637229Notes

Reaction equation

HRID 1637229 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[NH2:6][C:7]1[CH:12]=[C:11](Cl)[CH:10]=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:6][C:7]1[CH:12]=[C:11]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:10]=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 10013146HCID 10013146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

240 mmol of imidazole, 240 mmol of 2-amino4-chloronitrobenzene and 240 mmol of potassium carbonate in 450 ml of dimethylformamide (DMF) are stirred in a 1 litre round-bottomed flask. The mixture is maintained at 130° C. with stirring for 48 hours. After the DMF has been removed by evaporation, the residue is taken up in water. The precipitate that forms is filtered off and then washed with water. It is then dissolved in 550 ml of 1N hydrochloric acid. After insoluble material has been filtered off, the filtrate is rendered alkaline and the precipitate that forms is filtered off and washed with water. After drying, the expected product is obtained after purification by chromatography on silica gel using a dichloromethane/methanol mixture(95/5).

Workup

  1. customAfter the DMF has been removed by evaporation
  2. filtrationThe precipitate that forms is filtered off
  3. washwashed with water
  4. dissolutionIt is then dissolved in 550 ml of 1N hydrochloric acid
  5. filtrationAfter insoluble material has been filtered off
  6. filtrationthe precipitate that forms is filtered off
  7. washwashed with water
  8. customAfter drying

Sources & evidence

ORD record
ord-2849616f59764d5fa05b26f6ee33ea48
Source dataset
uspto-grants-2000_03
Patent number
US06040327

Reaction notes

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