Hydrazine → tert-Butyl 2-(2-hydrazinyl-2-oxoethyl)benzo[d]thiazole-6-carboxylate

HRID 1190850Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190850
C([O:3][C:4](=O)[CH2:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1)C.[NH2:23][NH2:24]>CO>[NH:23]([C:4](=[O:3])[CH2:5][C:6]1[S:7][C:8]2[CH:14]=[C:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1)[NH2:24]

Komponenten

4

Edukt 2

HCID 9321HydrazineHCID 86707744tert-Butyl 2-(2-ethoxy-2-oxoethyl)benzo[d]thiazole-6-carboxylate

Produkt 1

HCID 86707745tert-Butyl 2-(2-hydrazinyl-2-oxoethyl)benzo[d]thiazole-6-carboxylateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of Compound 188b (480 mg, 1.5 mmol) in methanol (15 mL) was added anhydrous hydrazine (0.19 mL, 6.0 mmol) and the mixture stirred for 16 h. The resulting precipitate was filtered, washed with three volumes of methanol and dried in vacuo to afford Compound 188c (400 mg, 87%) as white powder. LCMS=1.64 min using analytical method (B), 308.0 (M+H). 1H NMR (400 MHz, CD3OD) δ 8.59 (d, J=1.1 Hz, 1H), 8.08 (dd, J=8.6, 1.8 Hz, 1H), 8.02-7.97 (m, 1H), 1.63 (s, 9H).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with three volumes of methanol
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c6a990134a3a4dcd93bc4c38ceb8f097
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680090B2

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