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

HRID 1755279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755279
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

Komponenten

6

Edukt 2

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

Produkt 1

HCID 156230742-(2-methylphenyl)-4-thiazolecarboxylic acidAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-099503fd0f864c48adc491122df13b66
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169261B2

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