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

HRID 730700

Reaction equation

HRID 730700 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-04e9bb371a82400bb05f9ca6233dd47e
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Linked notes

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