1,1'-Carbonyldiimidazole → 5-Trifluoromethyl-1,3-dihydro-benzimidazol-2-one

HRID 912758Notes

Reaction equation

HRID 912758 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([NH2:10])[CH:4]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14]>C1COCC1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:13](=[O:14])[NH:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 5208224-Trifluoromethyl-1,2-phenylenediamine

Product 1

HCID 118201505-Trifluoromethyl-1,3-dihydro-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-trifluoromethyl-1,2-phenylenediamine (8.8 g, 50 mmol, Lancaster) and 1,1′-carbonyldiimidazole (9.0 g, 55 mmol, Aldrich) in THF (50 mL) was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with EtOAc to give the title compound. MS (ESI, pos. ion) m/z: 203 (M+1).

Workup

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

Sources & evidence

ORD record
ord-f5f514d5bc584525bdb7cb16d34b94d3
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

Loading…