Chlorosuccinimide → 1-(7-Isopropoxy-2-benzothiazolyl)-3-ethylurea
Reaktionsgleichung
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[O:17][CH:18]([CH3:20])[CH3:19].[Li]CCCC.ClN1C(=O)CCC1=O>COCCOC.CO>[CH:18]([O:17][C:3]1[C:4]2[S:8][C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])=[N:6][C:5]=2[CH:15]=[CH:16][CH:2]=1)([CH3:20])[CH3:19]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of 1-(6-bromo-7-isopropoxy-2-benzothiazolyl)-3-ethylurea (0.036 g, 0.10 mmol) in 0.5 mL DME was cooled down to about −78° C., and was treated with a solution of 1.6 M n-BuLi in hexanes (0.16 mL, 0.26 mmol, 2.6 eq). It was stirred at the temperature for about 20 min, then a solution of N-chlorosuccinimide (NCS) (0.015 g, 0.11 mmol, 1.1 eq) in 0.5 mL DME was added. It was warmed up to about 0° C. for about 0.5 hour. It was taken up in MeOH and purified by HPLC to give 0.007 g (25%) of the title compound. LC/MS 279.9 (M+1); LC retention time 3.10 min.
Aufarbeitung
- custompurified by HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-9a4c0e1c1fc94c6586402782e0c32725
- Quelldatensatz
- uspto-grants-2006_08
- Patentnummer
- US07091227B2
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