1,1'-Carbonyldiimidazole → HCID 59536332, compound

HRID 445373Notes

Reaction equation

HRID 445373 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:4][CH:3]=1.[C:13](N1C=CN=C1)([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:14]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][CH2:10][O:11][CH3:12])[C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22649666HCID 22649666, compound

Product 1

HCID 59536332HCID 59536332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a 50 mL round-bottomed flask was added 4-fluoro-N-(2-methoxyethyl)-benzenamine (512 mg, 3026 μmol, from step 1), 1,1′-carbonyldiimidazole (736 mg, 4539 μmol, Aldrich), THF (2 mL). The reaction mixture was stirred at 80° C. for 28 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 80% EtOAc/hexanes to give N-(4-fluoro-phenyl)-N-(2-methoxyethyl)-1H-imidazole-1-carboxamide. MS (ESI pos. ion) m/z: 264 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-b073cdf11a1f4eff821b19bc55dbdb9b
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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