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Ethyl Acetate → 6,7-Difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-1,3-dihydro-benzoimidazol-2-one

HRID 1914870
Notes
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Reaction equation

HRID 1914870 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[F:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([O:21][CH3:22])=[C:16]([NH2:23])[C:15]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=1[F:32].C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[F:20][C:19]1[CH:18]=[C:17]([O:21][CH3:22])[C:16]2[NH:23][C:1](=[O:2])[N:24]([C:25]3[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=3[F:32])[C:15]=2[C:14]=1[F:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 532609665,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine

Product 1

HCID 593863686,7-Difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-1,3-dihydro-benzoimidazol-2-oneYield 89.5%

Reagents, catalysts & solvents 2

HCID 6344Dichloromethane
Solvent
HCID 8058HexaneSolvent

Procedure

1,1′-Carbonyldiimidazole (4.68 g, 288 mmol) was added portion wise to a solution of 3,4-difluoro-N2-(2-fluoro-4-iodo-phenyl)-6-methoxy-benzene-1,2-diamine (I-5a: 6.3 g, 144 mmol) in DCM (60 mL) and the resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was filtered, the residue was washed with DCM and dried under reduced pressure to afford 6.0 g of the product (89.5% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue was washed with DCM
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-56ca29b17cb44bd5a7a7c9f0043204ea
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08614239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes