Potassium Carbonate → 4-chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline

HRID 277419Notes

Reaction equation

HRID 277419 reaction equation
[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>O1CCCC1>[Cl:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH:6][C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 141574954-Chloro-2-fluoro-5-methylaniline

Product 1

HCID 186156474-chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-fluoro-5-methylaniline (5 g, 31.4 mmol) was dissolved in tetrahydrofuran (100 ml) and potassium carbonate (6.0 g, 37.7 mmol) and phenyl chloroformate (5.9 g, 37.7 mmol) were added. Solution was refluxed for 3 hr and the solvent was removed under reduced pressure. Product was purified by column chromatography on silica gel (eluent, methylene chloride:hexane, 6:4; 7.15 g).

Workup

  1. temperatureSolution was refluxed for 3 hr
  2. customthe solvent was removed under reduced pressure
  3. customProduct was purified by column chromatography on silica gel (eluent, methylene chloride:hexane, 6:4; 7.15 g)

Sources & evidence

ORD record
ord-d595bbe22baf412790a9eff1fe0479c7
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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