Triethylamine → HCID 178444347, compound

Temperature

0 °C

428 mg of triethylammonium p-[trans-4-(trans-1-pentenyl)cyclohexyl]phenyldithiocarbamate were dissolved in 4 ml of chloroform and the solution was treated under argon with 284 μl of triethylamine. The mixture was subsequently cooled to 0° C. and treated dropwise with 194 μl of ethyl chloroformate. The mixture was stirred at 0° C. for a further 10 minutes and then at room temperature for 1 hour. The reaction mixture was subsequently partitioned between 100 ml of diethyl ether and 100 ml of water. The aqueous phase was back-extracted twice with 100 ml of diethyl ether each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the oily residue (450 mg) on 35 g of silica gel with ethyl acetate/petroleum ether (vol. 7:93) gave 234 mg (51%) of p-[trans-4-(trans-1-pentenyl)cyclohexyl]-phenyl isothiocyanate as colourless crystals. By recrystallization from 10 ml of methanol at 0° C. there were obtained 119 mg of p-[trans-4-(trans-1-pentenyl)cyclohexyl]phenyl isothiocyanate of melting point (C-I) 61.2° C. and cl.p. (N-I) 49.0° C.

1. waitat room temperature for 1 hour
2. customThe reaction mixture was subsequently partitioned between 100 ml of diethyl ether and 100 ml of water
3. extractionThe aqueous phase was back-extracted twice with 100 ml of diethyl ether each time
4. washThe organic phases were washed twice with 100 ml of water each time
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated

ORD record

ord-2effe564f95e4224a14b0caf6b12304a

Source dataset

uspto-grants-1990_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04980486