3-Phenoxyaniline → Methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate

HRID 1371079Notes

Reaction equation

HRID 1371079 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[O:13]([C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1CCCCC1.O.C(Cl)Cl>[O:13]([C:20]1[CH:21]=[C:22]([NH:23][CH2:2][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[CH:24]=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 771353-PhenoxyanilineHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 23506109Methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoateYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

EX-612A) Methyl 3-(bromomethyl)benzoate (7.2 g, 0.031 mol) was added dropwise to a solution of 3-phenoxyaniline (20.5 g, 0.11 mol) in 160 mL of cyclohexane. The reaction mixture was refluxed overnight then cooled to room temperature and diluted with water and methylene chloride. The layers were separated, and the aqueous layer was extracted with methylene chloride. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give a dark oil. The crude product was purified by reverse phase HPLC eluting with 20% to 90% acetonitrile in water to afford 6.2 g (59%) of the desired methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate product as a yellow oil. ESMS m/z=334 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto give a dark oil
  8. customThe crude product was purified by reverse phase HPLC
  9. washeluting with 20% to 90% acetonitrile in water

Sources & evidence

ORD record
ord-5ea277ce06114103a54b5d32af495216
Source dataset
uspto-grants-2003_06
Patent number
US06583183B2

Reaction notes

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