Sodium Hydroxide → 3-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic Acid

HRID 349437Notes

Reaction equation

HRID 349437 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:23]=[CH:22][CH:21]=[C:6]([C:7]([NH:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:12])=O)[CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:12][C:7]([C:6]3[CH:5]=[C:4]([CH:23]=[CH:22][CH:21]=3)[C:3]([OH:2])=[O:24])=[N:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58804856N-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-isophthalamic Acid Methylester

Product 1

HCID 588048453-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzoic AcidYield 92.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 1.7 g (5.5 mmol) N-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-isophthalamic acid methylester from Preparation 3 in a 3:1:1 mixture of THF/methanol/water was added 10 mL (10 mmol) 1N NaOH. The mixture was stirred 4 hours at room temperature before concentrating on a rotary evaporator. The residue was treated with 6M HCl then filtered, washed with water (1×) and dried in a vacuum oven overnight at 70° C. to provide 1.5 g (91%) desired product.

Workup

  1. concentrationbefore concentrating on a rotary evaporator
  2. additionThe residue was treated with 6M HCl
  3. filtrationthen filtered
  4. washwashed with water (1×)
  5. customdried in a vacuum oven overnight at 70° C.

Sources & evidence

ORD record
ord-0bec8faa9fc847f6b5eaeb87b451b8a4
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

Loading…