1,3-Dichloro-5,5-dimethylhydantoin → HCID 68697643, compound

HRID 2244368Notes

Reaction equation

HRID 2244368 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[NH:12][CH3:13])[CH3:2].[Cl:15]N1C(C)(C)C(=O)N(Cl)C1=O>C(O)(=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([Cl:15])[CH:8]=[C:7]([F:11])[C:6]=1[NH:12][CH3:13])[CH3:2]

Participants

5

Reactant 2

HCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 68696785HCID 68696785, compound

Product 1

HCID 68697643HCID 68697643, compoundYield 124%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-fluoro-2-methylaminobenzoic acid ethyl ester (124 mg, 0.63 mmol) in acetic acid (4 ml) was added 1,3-dichloro-5,5-dimethylhydantoin (93 mg, 0.47 mmol). The reaction mixture was stirred at RT for 3 h. The mixture was diluted with ethyl acetate and then washed with sat. NaHCO3. The organic phase was then washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography to give 5-chloro-3-fluoro-2-methylaminobenzoic acid ethyl ester (135 mg, 93%) as a yellow oil. 1H NMR (CDCl3, 300 MHz): 7.67 (dd, J=2.5, 1.5 Hz, 1H), 7.52 (brds, 1H), 7.09 (dd, J=13.5, 2.5 Hz, 1H), 4.31 (q, J=7.0 Hz, 2H), 3.11 (m, 3H), 1.38 (t, J=7.0 Hz, 3H).

Workup

  1. washwashed with sat. NaHCO3
  2. washThe organic phase was then washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-ddee2c5e122d409bac682c62f050a672
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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