1,3-Dichloro-2-isothiocyanatobenzene → HCID 18316179, Verbindung

N-Cyclohexyl-1,1-dimethyl-2-hydroxyethanamine was prepared in a manner analogous to Method B4a. A solution of 2,6-dichlorophenyl isothiocyanate (1.2 g, 6.0 mmol) and N-cyclohexyl-1,1-dimethyl-2-hydroxyethanamine (1.0 g, 6.0 mmol) in CH2Cl2 (10 mL) was stirred for 20 h at room temp. The resulting mixture was concentrated under reduced pressure, then treated with a 33% HCl solution (15 mL). The resulting mixture was heated at the reflux temp. for 1 h, cooled to room temp. and neutralized with a 45% NaOH solution. The resulting slurry was filtered, and the resulting solids were washed with water (20 mL), then recrystallized (EtOH) to yield 2-(2,6-dichlorophenylimino)-3-cyclohexyl-4,4-dimethyl-1,3-thiazolidine (0.70 g, 33%/o): mp 134° C. When appropriate, the product was converted into the HCl salt by dissolving the free base (5 mmol) in Et2O (50 mL) and treating this solution with a 2N ethereal HCl solution until no more solid precipitated. The resulting slurry was filtered and the resulting solids were washed with Et2O (25 mL) followed by EtOAc (25 mL).

1. concentrationThe resulting mixture was concentrated under reduced pressure
2. additiontreated with a 33% HCl solution (15 mL)
3. temperatureThe resulting mixture was heated at the reflux temp
4. temperaturecooled to room temp.
5. filtrationThe resulting slurry was filtered
6. washthe resulting solids were washed with water (20 mL)
7. customrecrystallized (EtOH)

ORD-Eintrag

ord-c9c145cf06f64feabc107217a566f25c

Quelldatensatz

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06353006B1