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

HRID 51892

Reaktionsgleichung

Reaktionsgleichung von HRID 51892
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[NH:18][C:19]([NH2:21])=[S:20].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:18]=[C:19]([NH2:21])[S:20][C:5]=2[C:6]([N:9]([CH3:17])[CH2:10][CH:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 22736994HCID 22736994, Verbindung

Produkt 1

HCID 227370054-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamineAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

1.5 g (0.53 mmol) {2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea were dissolved in 15 ml chloroform and at room temperature 0.025 ml (0.5 mmol) Br2 were added slowly. After 24 hrs of reflux the mixture was concentrated in vactio 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 (1/1 hexane/ethyl acetate) to afford 0.16 g (10%) of 4-methoxy-N7-methyl-N7-(tetrahydro-pyran-4-ylmethyl)-benzothiazole-2,7-diamine as brown solid. ES-MS m/e (%): 308 (M+H+, 100).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ff07b51b7c5147e79cbabb50bbbdd643
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713499B2

Verknüpfte Notizen

Wird geladen…