Methanol → 4-Phenylthiazole-2-carboxylic acid

HRID 2236175Notes

Reaction equation

HRID 2236175 reaction equation
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1)=[O:5])C.O1CCCC1.CO.[H-].[OH-].[Li+]>O>[C:11]1([C:9]2[N:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][CH:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24730326Ethyl 4-phenyl-1,3-thiazole-2-carboxylateHCID 86597229HCID 86597229, compound

Product 1

HCID 38785394-Phenylthiazole-2-carboxylic acidYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Phenyl-thiazole-2-carboxylic acid ethyl ester, commercially available from Pharma Core, (1.0 g, 4.28 mmol) in a mixture solution of tetrahydrofuran, methanol and water (3:1:1, 10 mL) was treated with lithium hydroxide monohydride (514 mg, 12.8 mmol) at room temperature for three hours. After the reaction was complete, solvent was evaporated. To the residue, water was added, and pH of the resulting solution was adjusted to ˜1-2 by addition of dilute hydrochloride acid (1N). The white precipitation was collected by centrifugation and further washed with water to give 4-phenyl-thiazole-2-carboxylic acid (473 mg, 54%). LCMS calcd for C10H7NO2S (m/e) 205, obsd 206 (M+H).

Workup

  1. customsolvent was evaporated
  2. additionTo the residue, water was added
  3. additionpH of the resulting solution was adjusted to ˜1-2 by addition of dilute hydrochloride acid (1N)
  4. customThe white precipitation
  5. customwas collected by centrifugation
  6. washfurther washed with water

Sources & evidence

ORD record
ord-2ebee532f3004a07ad165fa6ce91dc9d
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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