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

HRID 1280290Notes

Reaction equation

HRID 1280290 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. extractionand the 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-90d4628d8cc146efbfa47fddabe76308
Source dataset
uspto-grants-2002_09
Patent number
US06448295B1

Reaction notes

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