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

HRID 1265375Notes

Reaction equation

HRID 1265375 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-a2e6275f937846f2b8fc6283c4d089d1
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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