1,3-Dichloro-5,5-dimethylhydantoin → 2-Amino-5-chloro-3-fluoro-N-methoxy-N-methyl-benzamide

HRID 1497228Notes

Reaction equation

HRID 1497228 reaction equation
[NH2:1][C:2]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[Cl:15]N1C(C)(C)C(=O)N(Cl)C1=O>C(O)(=O)C>[NH2:1][C:2]1[C:13]([F:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 815074922-Amino-3-fluoro-N-methoxy-N-methyl-benzamide

Product 1

HCID 866830482-Amino-5-chloro-3-fluoro-N-methoxy-N-methyl-benzamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-amino-3-fluoro-N-methoxy-N-methyl-benzamide (765 mg, 3.86 mmol) in acetic acid (18 ml) was added 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (783 mg, 2.7 mmol) at room temperature. The orange solution was stirred over night and was then poured carefully onto ice/saturated NaHCO3-solution. The mixture was extracted with EtOAc and the combined extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 90:10-80:20) to afford the title compound (544 mg, 61%) as light brown solid. MS (ESI): 233.0 (M+H)+.

Workup

  1. additionwas then poured carefully onto ice/saturated NaHCO3-solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined extracts were washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 90:10-80:20)

Sources & evidence

ORD record
ord-4c743107b2644a8f9409bbc09f1e76cb
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…