Sodium Hydroxide → 2-[(2,6-Dichlorophenyl)amino]-5-(3-phenoxybenzyl)benzene acetic acid

HRID 467295Notes

Reaction equation

HRID 467295 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][C:5]1[CH:10]=[C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:25][C:26]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:33].[OH-].[Na+]>O1CCOCC1>[Cl:32][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:33])[C:26]=1[NH:25][C:6]1[CH:7]=[CH:8][C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:13]=2)=[CH:10][C:5]=1[CH2:4][C:3]([OH:34])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57083598HCID 57083598, compound

Product 1

HCID 1317176002-[(2,6-Dichlorophenyl)amino]-5-(3-phenoxybenzyl)benzene acetic acidYield 43.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the ester (2.2 g, 4.3 mmol) of Step A in dioxane (20 mL) containing 1N NaOH (7 mL) is heated at reflux under nitrogen for 4 hrs. The solvent is removed and the residue is partitioned between dilute HCl and ether (30 mL each). The organic phase is washed with brine, dried (Na2SO4) and filtered. The filtrate is treated with tris(hydroxymethyl)aminomethane (0.485 g) in methanol (20 mL). The solvent is evaporated to a syrup in vacuo and diluted with ethyl acetate. The crystalline solid is collected (white solid, 1.6 g, 60%) and recrystallized from methanol-water to provide the pure title compound (0.89 g, m.p. 137°-138° C.).

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 4 hrs
  3. customThe solvent is removed
  4. customthe residue is partitioned between dilute HCl and ether (30 mL each)
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. additionThe filtrate is treated with tris(hydroxymethyl)aminomethane (0.485 g) in methanol (20 mL)
  9. customThe solvent is evaporated to a syrup in vacuo
  10. additiondiluted with ethyl acetate
  11. customThe crystalline solid is collected (white solid, 1.6 g, 60%)
  12. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-03c7e76b8418494989e5eb78e5672705
Source dataset
uspto-grants-1992_10
Patent number
US05159085

Reaction notes

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