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

HRID 240961

Reaction equation

HRID 240961 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-b0cc7e88d5ef48c78fc254f7c1f0edab
Source dataset
uspto-grants-2014_02
Patent number
US08648116B2

Linked notes

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