1,1'-Carbonyldiimidazole → HCID 59333298, compound

HRID 1893438Notes

Reaction equation

HRID 1893438 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[C:6]([NH2:8])[CH:7]=1.[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>C1C(Cl)=CC=C(Cl)C=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14](=[O:15])[NH:8]2

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 24700976HCID 24700976, compound

Product 1

HCID 59333298HCID 59333298, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 46851,4-DichlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2-imidazol-1-yl-phenylamine (5.00 g; 21 mmol; 1 eq) in anhydrous dichlorobenzene (410 mL), is added carbonyldiimidazole (6.94 g; 42 mmol; 2 eq) under argon atmosphere. This reaction mixture is allowed to stir under reflux for 2 hours. The initial crystal clear solution quickly turns black after heating and become non homogeneous. This crude reaction mixture is allowed to cool to room temperature and the grey powder formed during the reaction is filtered off on a fritted glass. The filtrate is cooled down to 0° C. overnight to afford a second batch of grey powder. The combined 6.5 g of grey solid is transferred in a 1 L flask, diluted in fresh ethyl acetate (500 mL) and heated to gentle reflux for ten minutes. Hot filtration followed by concentration afforded the title compound as a grey powder (3.85 g; 14.6 mmol; 69%).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe initial crystal clear solution quickly turns black after heating
  3. customThis crude reaction mixture
  4. customthe grey powder formed during the reaction
  5. filtrationis filtered off on a fritted glass
  6. temperatureThe filtrate is cooled down to 0° C. overnight
  7. customto afford a second batch of grey powder
  8. temperatureheated
  9. temperatureto gentle reflux for ten minutes
  10. filtrationHot filtration
  11. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-6c1c076071da4d3fa728d903770cb298
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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