Bromine → 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-yl)-benzothiazole-2,7-diamine

HRID 51900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51900
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:16])[CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:5][C:4]=1[NH:17][C:18]([NH2:20])=[S:19].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:17]=[C:18]([NH2:20])[S:19][C:5]=2[C:6]([N:9]([CH3:16])[CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 22736964HCID 22736964, Verbindung

Produkt 1

HCID 227369724-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-yl)-benzothiazole-2,7-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

0.28 g (0.95 mmol) {2-methoxy-5-[methyl-(tetrahydro-pyran-4-yl)-amino]-phenyl}-thiourea were dissolved in 15 ml chloroform and 0.05 ml (1.0 mmol) Br2 were added slowly at room temperature. After 24 hrs of reflux the mixture was concentrated in vacuo and the residue suspended in water. Sodium bicarbonate solution was added until the pH was 10, and the crystals were collected by filtration. These were subjected to column chromatography (ethyl acetate) to afford 0.41 g (41 (%o) of 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-yl)-benzothiazole-2,7-diamine as an off-white solid. ES-MS m/e (%): 294 (M+H+, 100).

Aufarbeitung

  1. temperatureAfter 24 hrs of reflux the mixture
  2. concentrationwas concentrated in vacuo
  3. additionSodium bicarbonate solution was added until the pH was 10
  4. filtrationthe crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-59fd7442ae8140d9aac8419bf3f93351
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713499B2

Notizen zur Reaktion

Wird geladen…