Sodium Hydroxide → 4-Methyl-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acid

HRID 1918536

Reaction equation

HRID 1918536 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>O.C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 3776504Ethyl 4-Methyl-2-(4-methylphenyl)thiazole-5-carboxylate

Product 1

HCID 27636254-Methyl-2-(4-methylphenyl)-1,3-thiazole-5-carboxylic acidYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The mixture of ethyl 4-methyl-2-p-tolylthiazole-5-carboxylate (0.200 g; 0.765 mmol) and sodium hydroxide (0.0643 g; 1.61 mmol) in water (4 mL) and ethanol (8 mL) was irradiated in a microwave oven at 130° C. for 5 min. The mixture was concentrated (removal of ethanol), and the pH of the solution was adjusted to 3 by addition of 6N hydrochloric acid. The acidic solution was extracted with (3×10 mL) of ethyl acetate. Combined organic layers were dried over magnesium sulfate, and evaporated to afford 0.157 g (88%) of 4-methyl-2-p-tolylthiazole-5-carboxylic acid as a white solid which was directly used in the next step.

Workup

  1. customwas irradiated in a microwave oven at 130° C. for 5 min
  2. concentrationThe mixture was concentrated
  3. custom(removal of ethanol)
  4. additionthe pH of the solution was adjusted to 3 by addition of 6N hydrochloric acid
  5. extractionThe acidic solution was extracted with (3×10 mL) of ethyl acetate
  6. dry with materialCombined organic layers were dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-accc9a20573c4895acf448fdd8a72d63
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Linked notes

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