Tetrahydrofuran → 2-Azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid

HRID 1667666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667666
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]=[N+:12]=[N-:13])=[N:8][C:7]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[O:5])C.O1CCCC1.O.[OH-].[Li+]>O.C(OCC)C>[N:11]([C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=2)[N:8]=1)=[N+:12]=[N-:13]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 866427982-Azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 866427992-Azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acidAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a mixture of 2.44 g (7.14 mmole) of 2-azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester and 45 mL of tetrahydrofuran was added, 3.01 g (71.5 mmole) of lithium hydroxide monohydrate in 33 mL of water. The mixture was stirred at room temperature for 17 hours and then diluted with 300 mL of diethyl ether. The ether layer was extracted three times with 100 mL of water. The combined aqueous phases were acidified by the addition of 1M hydrochloric acid and extracted three times with 100 mL of ethyl acetate. The combined ethyl acetate layers were washed with 50 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1.76 g of 2-azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid as a light yellow solid.

Aufarbeitung

  1. additionwas added
  2. extractionThe ether layer was extracted three times with 100 mL of water
  3. additionThe combined aqueous phases were acidified by the addition of 1M hydrochloric acid
  4. extractionextracted three times with 100 mL of ethyl acetate
  5. washThe combined ethyl acetate layers were washed with 50 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1682cf2e18914fe2bf306925308f9e7e
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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