1,1'-Carbonyldiimidazole → 4,6,7-Trifluoro-1-(2-Fluoro-4-iodo-phenyl)-1,3-dihydrobenzoimidazole-2-one

HRID 424004Notes

Reaction equation

HRID 424004 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-])=O)=[C:14]([F:19])[CH:13]=[C:12]([F:20])[C:11]=1[F:21].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>C(Cl)Cl>[F:19][C:14]1[C:15]2[NH:16][C:22](=[O:23])[N:9]([C:3]3[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=3[F:1])[C:10]=2[C:11]([F:21])=[C:12]([F:20])[CH:13]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

Product 1

HCID 593863794,6,7-Trifluoro-1-(2-Fluoro-4-iodo-phenyl)-1,3-dihydrobenzoimidazole-2-oneYield 65.85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the stirred solution of 3,4,6-trifluoro-N2-(2-Fluoro-4-iodo-phenyl)-benzene-1,2-diamine 3 (0.285 gm, 0.74 mmol) in CH2Cl2 (2 ml), 1,1′-carbonyldiimidazole (0.125 gm, 0.75 mmol) was added. This reaction mixture was kept stirring at room temperature for 16 hours when product precipitated out. The white solid was filtered and used further without any purification. (0.2 gm, yield: 65.85%): m/z=407 [M−1]−.

Workup

  1. customprecipitated out
  2. filtrationThe white solid was filtered
  3. customused further without any purification

Sources & evidence

ORD record
ord-0a997fbe1c184cc28e037b05fd94e7dc
Source dataset
uspto-grants-2012_01
Patent number
US08101799B2

Reaction notes

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