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

HRID 2405599Notes

Reaction equation

HRID 2405599 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 stifling 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. customwhen product precipitated out
  2. filtrationThe white solid was filtered
  3. customused further without any purification

Sources & evidence

ORD record
ord-3b269b0c32ac477db7b9078edfb18987
Source dataset
uspto-grants-2014_08
Patent number
US08808742B2

Reaction notes

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