Methylthiourea → 2-Methylamino-5,6-dihydro-4H-benzothiazol-7-one

HRID 2102780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2102780
Br[CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:10][NH:11][C:12]([NH2:14])=[S:13]>N1C=CC=CC=1>[CH3:10][NH:11][C:12]1[S:13][C:2]2[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[N:14]=1

Komponenten

4

Edukt 2

HCID 2723704MethylthioureaHCID 27704762-Bromocyclohexane-1,3-dione

Produkt 1

HCID 34274902-Methylamino-5,6-dihydro-4H-benzothiazol-7-oneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-cyclohexane-1,3-dione (8.0 g, 41.9 mmol) and methyl thiourea (3.77 g, 41.9 mmol) in pyridine (63 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under vacuum, extracted with CH2Cl2 /10% aq NaCl solution, dried, filtered, and concentrated under vacuum. Crystallization from EtOAc afforded the title compound as yellow crystals (3.26 g, 43%): mp 180-182° C. Anal. RP-HPLC: tR 8.4 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 7.90 (s, 1H, NH), 2.99 (s, 3H, CH3), 2.72 (t, 2H, J 6.1, CH2), 2.49 (t, 2H, J 6.1, CH2), 2.10 (qu, 2H, J 6.1, CH2). 13C-NMR (CDCl3): δ 191.0, 176.6, 168.0, 120.0, 37.5, 32.5, 27.7, 23.2. MS: (ESI+) m/z 183.07 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractionextracted with CH2Cl2 /10% aq NaCl solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customCrystallization from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-3a878cd7311a4754a19f1aa0345b618a
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576091B2

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