1,1'-Carbonyldiimidazole → HCID 59198750, compound

HRID 72745Notes

Reaction equation

HRID 72745 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[CH2:14][CH2:15][C:16]([O:18]CC)=[O:17].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>ClC1C=CC=CC=1Cl>[CH3:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[N:9]1[C:10]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:11][CH:12]=[C:13]1[C:21](=[O:22])[NH:1]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59198558Ethyl 1-(2-amino-4-methylphenyl)-1H-imidazole-2-propanoate

Product 1

HCID 59198750HCID 59198750, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Ethyl 3-[1-(2-amino-4-methylphenyl)-1H-imidazol-2-yl]-propanoate as synthesized in above Example 181, 160 mg, 1,1′-carbonyldiimidazole 143 mg and 1,2-dichlorobenzene 6 mL were mixed and heated under reflux for 1.5 hours. The reaction liquid was allowed to cool off, and the precipitate was recovered by filtration and washed with ethyl acetate. After being dried under reduced pressure, the product was mixed with 3 mL of ethanol and 3.0 mL of 1N aqueous sodium hydroxide solution and heated under reflux for 20 minutes. Cooling the reaction liquid off, 3.0 mL of 1N hydrochloric acid was added. The precipitated crystals were recovered by filtration, washed with water and dried in flowing air under heating to provide 82 mg of the title compound.

Workup

  1. additionwere mixed
  2. temperatureheated
  3. temperatureunder reflux for 1.5 hours
  4. customThe reaction liquid
  5. temperatureto cool off
  6. filtrationthe precipitate was recovered by filtration
  7. washwashed with ethyl acetate
  8. customAfter being dried under reduced pressure
  9. additionthe product was mixed with 3 mL of ethanol and 3.0 mL of 1N aqueous sodium hydroxide solution
  10. temperatureheated
  11. temperatureunder reflux for 20 minutes
  12. temperatureCooling
  13. customthe reaction liquid off, 3.0 mL of 1N hydrochloric acid
  14. additionwas added
  15. filtrationThe precipitated crystals were recovered by filtration
  16. washwashed with water
  17. customdried
  18. temperatureunder heating

Sources & evidence

ORD record
ord-177b4ef5bf5b4ee78909d982ad172e5f
Source dataset
uspto-grants-2014_09
Patent number
US08829000B2

Reaction notes

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