Reaktion #472372

Reaktionsgleichung

iodine

Carbon disulfide

trans-4-(aminomethyl)cyclohexanecarboxylic acid

triethylamine

hydrochloric acid

→

trans-4-(isothiocyanatomethyl)cyclohexanecarboxylic acid

Ausbeute 101.0%

Lösungsmittel

tetrahydrofuran

water

tetrahydrofuran

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe obtained reaction mixture
2. 2
   workup.STIRRINGby stirring at 0° C. for further two hours
3. 3
   workup.ADDITIONmixed
4. 4
   Sonstigethe organic layer was separated
5. 5
   Einengenconcentrated under reduced pressure to dryness
6. 6
   workup.ADDITIONTo the obtained residue, a solvent mixture of hexane (3 mL) and ethyl acetate (3 mL)
7. 7
   workup.ADDITIONwas added
8. 8
   workup.ADDITIONthoroughly mixed
9. 9
   Filtrationthe insoluble matter was filtered off
10. 10
    EinengenThen, the filtrate was concentrated under reduced pressure to dryness

Vorschrift

Carbon disulfide (0.26 mL, 4.4 mmol) was added to a mixture comprising trans-4-(aminomethyl)cyclohexanecarboxylic acid (0.24 g, 1.5 mmol), tetrahydrofuran (1.0 mL), water (1.0 mL) and triethylamine (0.51 mL, 3.6 mmol), followed by stirring at room temperature for 44 hours. The obtained reaction mixture was dropwise added to a tetrahydrofuran (1.0 mL) solution of iodine (0.41 g, 1.6 mmol) over a period of 5 minutes at 0° C., followed by stirring at 0° C. for further two hours. Thereafter, 1M hydrochloric acid (1.5 mL) was added and mixed. Then, ethyl acetate (6 mL) was added, and the organic layer was separated and concentrated under reduced pressure to dryness. To the obtained residue, a solvent mixture of hexane (3 mL) and ethyl acetate (3 mL) was added and thoroughly mixed, and the insoluble matter was filtered off. Then, the filtrate was concentrated under reduced pressure to dryness to obtain trans-4-(isothiocyanatomethyl)cyclohexanecarboxylic acid as a ocher solid (0.30 g, yield: 101%, and 1H-NMR spectrum showed no distinct by-product). LC-MS ES-198(retention time: 20.3 min, condition 3).

Quelle