Pyridine → 5-(2-Methoxyethylsulfonamido)-2-methylbenzoxazole

HRID 344992

Reaktionsgleichung

Reaktionsgleichung von HRID 344992
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.N1C=CC=CC=1.[CH3:18][O:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>C(OCC)(=O)C>[CH3:18][O:19][CH2:20][CH2:21][S:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1)(=[O:24])=[O:23]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7379202-Methyl-1,3-benzoxazol-5-amineHCID 134802212-Methoxyethane-1-sulfonyl chloride

Produkt 1

HCID 199934555-(2-Methoxyethylsulfonamido)-2-methylbenzoxazoleAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a 1.0 L round bottom flask equipped with mechanical stirrer, addition funnel, thermometer and nitrogen inlet tube was placed 100 grams (0.67 Mol) of 5-amino-2-methylbenzoxazole and 350 mL of pyridine. The slurry was stirred in an ice/ethanol bath at 0° C. then 110 grams (0.69 Mol) of Intermediate 1 was added dropwise so as to maintain a reaction temperature below 7° C. The reaction was stirred at 0° C. for two hours then the resulting red colored mixture was poured into 1.0 L of ethyl acetate. The slurry was stirred for 30 minutes then filtered and the collected solids were discarded. The filtrate was extracted with 4×200 mL of 10% hydrochloric acid and the organic phase was collected and dried over magnesium sulfate. The solvents were removed in vacuo to afford 140 grams (0.52 Mol, 76.7% yield) of desired product as a tan solid.

Aufarbeitung

  1. customInto a 1.0 L round bottom flask equipped with mechanical stirrer, addition funnel
  2. customthermometer and nitrogen inlet tube was placed
  3. temperatureto maintain a reaction temperature below 7° C
  4. stirringThe reaction was stirred at 0° C. for two hours
  5. stirringThe slurry was stirred for 30 minutes
  6. filtrationthen filtered
  7. extractionThe filtrate was extracted with 4×200 mL of 10% hydrochloric acid
  8. customthe organic phase was collected
  9. dry with materialdried over magnesium sulfate
  10. customThe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19827993b15d4df4943b33a9907b492b
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055387

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