Ethyl isocyanate → 1-(5-Bromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

HRID 2068704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068704
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.[CH2:14]([N:16]=[C:17]=[O:18])[CH3:15]>O1CCOCC1>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]2[S:9][C:8]([NH:10][C:17]([NH:16][CH2:14][CH3:15])=[O:18])=[N:7][C:6]=2[CH:11]=1

Komponenten

4

Edukt 2

HCID 8022Ethyl isocyanateHCID 129396805-Bromo-6-methoxybenzo[d]thiazol-2-amine

Produkt 1

HCID 596030851-(5-Bromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-bromo-6-methoxybenzo[d]thiazol-2-amine V (2.0 g, 7.72 mmol) in 1,4-dioxane (20.0 mL) was added ethylisocyanate (3.0 mL, 38.60 mmol) and heated the resulting reaction mixture to 80° C. for 16 h. After the completion of the reaction (TLC monitoring), 1,4-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 90° C. for 2 h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (2.10 g, 83%). 1H NMR (400 MHz, DMSO-d6): δ 1.07 (t, J=7.20 Hz, 3H), 3.17 (quintet, J=6.80 Hz, 2H), 3.86 (s, 3H), 6.65 (br s, 1H), 7.68 (s, 1H), 7.80 (s, 1H) and 10.67 (br s, 1H). MS: 330.08 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. customthe resulting reaction mixture to 80° C. for 16 h
  3. distillationwas distilled off
  4. filtrationfollowed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b184b2b19aba490d87059b6a59098a30
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299065B2

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