Nitric Acid → 6,7-Difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-5-nitro-1,3-dihydro-benzoimidazol-2-one

HRID 1914872Notes

Reaction equation

HRID 1914872 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:21][CH3:22])[C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]3[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=3[F:18])[C:6]=2[C:19]=1[F:20].[N+:23]([O-])([OH:25])=[O:24].C(OCC)(=O)C>CCCCCC>[F:1][C:2]1[C:3]([N+:23]([O-:25])=[O:24])=[C:4]([O:21][CH3:22])[C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]3[CH:16]=[CH:15][C:14]([I:17])=[CH:13][C:12]=3[F:18])[C:6]=2[C:19]=1[F:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 593863686,7-Difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 672398796,7-Difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-5-nitro-1,3-dihydro-benzoimidazol-2-oneYield 48.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

6,7-Difluoro-1-(2-fluoro-4-iodo-phenyl)-4-methoxy-1,3-dihydro-benzoimidazol-2-one (3.0 g, 7.14 mmol) was added portion wise to fuming nitric acid at −78° C. over a period of 1 minute and the resulting mixture was stirred at room temperature for 5 minutes. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was quenched with cold water. The solid formed was collected, washed with water and dried to give the crude product. Purification by column chromatography on silica gel (10-40% ethyl acetate in hexane) afforded 1.6 g of the product (48.2% yield).

Workup

  1. customThe reaction mixture was quenched with cold water
  2. customThe solid formed
  3. customwas collected
  4. washwashed with water
  5. customdried
  6. customto give the crude product
  7. customPurification by column chromatography on silica gel (10-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c11abe1f14b0468f980b78994ff55453
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

Loading…