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

HRID 349441Notes

Reaction equation

HRID 349441 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[CH:5]=1.[OH-].[Na+]>C1COCC1.CO.O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[S:11][C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:23])=[O:2])=[N:14][CH:13]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 588048543-[5-(4-Methoxy-phenyl)-thiazol-2-yl]-benzoic acid methyl ester

Product 1

HCID 588048623-[5-(4-Methoxy-phenyl)-thiazol-2-yl]-benzoic AcidYield 89.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 1.4 g (4.3 mmol) 3-[5-(4-Methoxy-phenyl)-thiazol-2-yl]-benzoic acid methyl ester from Preparation 10 in a 3:1:1 mixture of THF/methanol/water was added 10 mL (10 mmol) 1N NaOH. The mixture was stirred 14 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 1.2 g (88%) of 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-6befcc308a424cb9abd2e94686cfc018
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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