2-Bromo-1,1-dimethoxyethane → 2-(4-(Trifluoromethyl)phenyl)thiazole

HRID 1460995

Reaktionsgleichung

Reaktionsgleichung von HRID 1460995
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](=[S:9])[NH2:8])=[CH:5][CH:4]=1.CO[CH:16](OC)[CH2:17]Br>Cl.C(O)C>[F:13][C:2]([F:12])([F:1])[C:3]1[CH:11]=[CH:10][C:6]([C:7]2[S:9][CH:16]=[CH:17][N:8]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 27348234-(Trifluoromethyl)thiobenzamide

Produkt 1

HCID 146019692-(4-(Trifluoromethyl)phenyl)thiazoleAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred solution of 5.0 grams (0.024 mole) of 4-trifluoromethylbenzthioamide, 4.4 grams (0.026 mole) of bromoacetaldehyde dimethyl acetal, and 4 drops of concentrated hydrochloric acid in 50 ml of ethanol was heated at reflux for 18 hours. After this time the reaction mixture was subjected to column chromatography on silica gel. Elution was accomplished using 20% ethyl acetate in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 3.3 grams of 2-(4-trifluoromethylphenyl)thiazole. The nmr spectrum was consistent with the proposed structure. The reaction was repeated several times.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. washElution
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-52935fdb1b064cff904a505076b8fd46
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05073564

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