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2,4-Dimethylthiazole → 5-(2-Methoxy-4-nitro-phenyl)-2,4-dimethyl-thiazole

HRID 1855506
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1855506
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].C([O-])(=O)C.[K+].[CH3:18][C:19]1[S:20][CH:21]=[C:22]([CH3:24])[N:23]=1>CN(C)C(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:21]1[S:20][C:19]([CH3:18])=[N:23][C:22]=1[CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 109342,4-DimethylthiazoleHCID 1012932-Bromo-5-nitroanisoleHCID 517044Potassium Acetate

Produkt 1

HCID 670961295-(2-Methoxy-4-nitro-phenyl)-2,4-dimethyl-thiazoleAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

In a microwave vial a mixture of 2-bromo-5-nitroanisole (600 mg, 2.53 mmol), potassium acetate (377 mg, 3.80 mmol) and tetrakis(triphenylphosphine)-palladium(0) (148 mg, 0.13 mmol) in N,N-dimethylacetamide (8 mL) was flushed with nitrogen while 2,4-dimethylthiazole (1.47 g, 12.6 mmol) was added. The tube was sealed and the mixture irradiated for 30 minutes at 170° C. The red-brown mixture was partitioned between ethyl acetate and water. The aqueous layer was re-extracted with ethyl acetate. The combined organic phases were washed with water, with brine, dried with magnesium sulfate and the solvent was evaporated to dryness. Column chromatography (40 g silica, heptane/ethyl acetate 7/3) afforded the title compound (415 mg, 62%) as a yellow solid. MS ISP (m/e): 265.1 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.90 (dd, 1H), 7.81 (d, 1H), 7.45 (d, 1H), 3.95 (s, 3H), 2.71 (s, 3H), 2.35 (s, 3H). Mp 123-125° C.

Aufarbeitung

  1. additionwas added
  2. customThe tube was sealed
  3. customthe mixture irradiated for 30 minutes at 170° C
  4. customThe red-brown mixture was partitioned between ethyl acetate and water
  5. extractionThe aqueous layer was re-extracted with ethyl acetate
  6. washThe combined organic phases were washed with water, with brine
  7. dry with materialdried with magnesium sulfate
  8. customthe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-634e082876a54969ac91c4bd2ffdb525
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962834B2

Notizen zur Reaktion

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