Sodium Hydroxide → 2-(2-methylphenyl)-4-thiazolecarboxylic acid

HRID 1755279Notes

Reaction equation

HRID 1755279 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CO.C(Cl)Cl>[C:12]1([CH3:17])[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53403771Ethyl 2-(2-methylphenyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 156230742-(2-methylphenyl)-4-thiazolecarboxylic acidYield 89.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-o-Tolyl-thiazole-4-carboxylic acid ethyl ester (550 mg, 2.22 mmol) was dissolved in a mixture of THF (1.0 mL) and MeOH (1.0 mL). To this was added NaOH (20% aqueous, 0.444 mL). The reaction mixture was stirred overnight and was then diluted with CH2Cl2 (30 mL) and washed with 1M NaHSO4 (30 mL). The aqueous layer was extracted with CH2Cl2 (2×30 mL), then the combined organic layers were washed with water (1×30 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the product (434 mg, 1.98 mmol, 89%) as a white solid.

Workup

  1. washwashed with 1M NaHSO4 (30 mL)
  2. extractionThe aqueous layer was extracted with CH2Cl2 (2×30 mL)
  3. washthe combined organic layers were washed with water (1×30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-099503fd0f864c48adc491122df13b66
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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