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

HRID 2076126

Reaktionsgleichung

Reaktionsgleichung von HRID 2076126
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) was flushed with argon while 2-methylthiazole (1.71 g, 16.9 mmol) was added. The tube was sealed and the mixture was irradiated 2 times for 30 minutes in a microwave oven 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 (100) [(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 was irradiated 2 times for 30 minutes in a microwave oven 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-7a1eab6efdcc440786e15bbe5a6c7e56
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923450B2

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