Bis-(1H-imidazol-2-YL)-methanone → 4-fluoro-1-(2-fluorophenyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 2246752Notes

Reaction equation

HRID 2246752 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:3]=1[NH2:16].[C:17](C1NC=CN=1)(C1NC=CN=1)=[O:18]>O1CCCC1>[F:1][C:2]1[C:3]2[NH:16][C:17](=[O:18])[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[F:15])[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 607889403-fluoro-N1-(2-fluorophenyl)benzene-1,2-diamine

Product 1

HCID 685301964-fluoro-1-(2-fluorophenyl)-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-fluoro-N1-(2-fluorophenyl)benzene-1,2-diamine (0.44 g, 2 mmol) and carbonyl diimidazole (0.29 g, 1.8 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature overnight. Upon disappearance of the starting material, the reaction was partitioned between 1 N hydrochloric acid (100 mL) and ethyl acetate (100 mL). The organics were dried over sodium sulfate and concentrated to give 4-fluoro-1-(2-fluorophenyl)-1,3-dihydro-2H-benzimidazol-2-one as a white solid in near quantitative yield. MS (ES) m/z 247.0

Workup

  1. customUpon disappearance of the starting material, the reaction was partitioned between 1 N hydrochloric acid (100 mL) and ethyl acetate (100 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-10bf41f890bd4ed89ff0002456fa3741
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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