2-Methylthiazole → 5-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazole

HRID 1855503

Reaktionsgleichung

Reaktionsgleichung von HRID 1855503
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]=[CH:22][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][CH:22]=1

Komponenten

6

Edukt 3

HCID 771292-MethylthiazoleHCID 1012932-Bromo-5-nitroanisoleHCID 517044Potassium Acetate

Produkt 1

HCID 670963525-(2-Methoxy-4-nitro-phenyl)-2-methyl-thiazoleAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

In a microwave vial a mixture of 2-bromo-5-nitroanisole (800 mg, 3.38 mmol), potassium acetate (503 mg, 5.07 mmol) and tetrakis(triphenylphosphine)-palladium(0) (197 mg, 0.17 mmol) in N,N-dimethylacetamide (12 mL) were flushed with argon while 2-methylthiazole (1.71 g, 16.9 mmol) was added. The tube was sealed and the mixture irradiated two times for 30 minutes at 160° C. The red-brown mixture was partitioned between ethyl acetate and water. The water layer was re-extracted with ethyl acetate. The combined organic phases were washed three times with water, once with brine, dried with magnesium sulfate and evaporated to dryness. Column chromatography (70 g silica, heptane/ethyl acetate 7:3 v/v) afforded the title compound (360 mg, 42%) as a yellow solid. MS ISP (m/e): 251.1 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.15 (s, 1H), 7.90 (dd, 1H), 7.84 (s, 1H), 7.72 (d, 1H), 4.05 (s, 3H), 2.76 (s, 3H). Mp 114-117° C.

Aufarbeitung

  1. additionwas added
  2. customThe tube was sealed
  3. customthe mixture irradiated two times for 30 minutes at 160° C
  4. customThe red-brown mixture was partitioned between ethyl acetate and water
  5. extractionThe water layer was re-extracted with ethyl acetate
  6. washThe combined organic phases were washed three times with water
  7. dry with materialonce with brine, dried with magnesium sulfate
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-59722fd22d2b444ca30c33e4a0d2bbe5
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962834B2

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