Cesium carbonate → HCID 178483328, Verbindung

N,N-dimethylglycine hydrazide hydrochloride (50 g, 0.263 mol) was stirred for 5 min in EtOH (525 mL). To this suspension was added Cs2CO3 (62.5 g, 0.192 mol) and the mixture was stirred at room temperature for 15 min. Methyl isothiocyanate (19.25 g, 0.263 mol) in EtOH (270 mL) was added to the pot and the reaction mixture was brought to reflux. The reflux condenser was removed and the EtOH was allowed to evaporate under atmospheric pressure (oil bath temperature 105–110° C.) over 3 h to give a purple paste. The reaction was removed from heat and allowed to sit at room temperature overnight (18 h), during which time the paste became a solid. The solid was mixed with CH2Cl2 (1.5 L) and filtered. The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil. The oil was purified by column chromatography through silica gel, eluting with 4:1 CH2Cl2/MeOH to afford 15.3 g (34.9%) of the desired product.

1. temperatureto reflux
2. customThe reflux condenser was removed
3. customto evaporate under atmospheric pressure (oil bath temperature 105–110° C.) over 3 h
4. customto give a purple paste
5. customThe reaction was removed
6. temperaturefrom heat
7. waitto sit at room temperature overnight
8. custom(18 h)
9. additionThe solid was mixed with CH2Cl2 (1.5 L)
10. filtrationfiltered
11. concentrationThe organic filtrate was concentrated under reduced pressure
12. customto give 31 g of a crude yellow oil
13. customThe oil was purified by column chromatography through silica gel
14. washeluting with 4:1 CH2Cl2/MeOH

ORD-Eintrag

ord-31ecad0905d1462eac13c90fffd1b8d5

Quelldatensatz

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07148226B2