Dimethyl Sulfate → Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

HRID 1373194Notes

Reaction equation

HRID 1373194 reaction equation
[F:1][C:2]1[C:3]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[C:4]([CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]=1[F:11])[C:5]([OH:7])=[O:6].[C:24](=O)(O)[O-].[Na+].COS(OC)(=O)=O.CCCCCC>CC(C)=O.CCOC(C)=O>[CH3:24][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[C:10]([F:11])=[C:2]([F:1])[C:3]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=1[F:23]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 210742923,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoic acid

Product 1

HCID 58781115Methyl 3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)-5-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-5-nitro-benzoic acid (595.3 g, 1.363 mol) in acetone (9 L) was added sodium bicarbonate (609.0 g, 3.48 mol) and the mixture was stirred for 10 min. To this suspension was added dimethylsulfate (285.6 ml, 3.026 mol) and refluxed for 3 h (completion of reaction was confirmed by TLC-hexane: EtOAc/4:1), cooled to room temperature and evaporated under vacuum. The residue (yellow) was further digested in hot methanol (2 L), filtered, washed with methanol and dried to give the title compound as a solid (yellow). Yield: 405.63g (65.54%).

Workup

  1. temperaturerefluxed for 3 h
  2. customevaporated under vacuum
  3. filtrationfiltered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-558c4bb42bc54c82a1524ebc74602d7d
Source dataset
uspto-grants-2007_01
Patent number
US07160915B2

Reaction notes

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