Thiophosgene → HCID 86749817, compound

Participants

Reaction Steps

To a round bottom flask containing the aniline 24 (28.8 mg, 0.0487 mmol) and dichloromethane (10 mL) was added 0.2211 M solution of thiophosgene (0.22 mL, 0.0509 mmol) in dichloromethane. The heterogeneous reaction mixture was stirred at room temperature for 1 hour and the solvent was removed in vacuo. Flash chromatography of this crude product using 100% EtOAc gave the isothiocyanate 25 as a clear oil (18.9 mg, 61.3% yield). 1H NMR (in CDCl3): δ7.17 (d,j=8.5 Hz,4H,2H3 &H5 --Ar--OCH3), 7.07 (m,2H,2NH--CO), 6.82 (d,j=8.5 Hz,4H,2H2 &H6 --Ar--OCH3), 3.78 (s,6H, 2CH3O), 3.70 (s,4H,2S--CH2 --Ar), 3.49 (t,j=5.9 Hz,2H,N--CH2CH2 -NCS ), 3.21 (q,j=6.2 Hz,4H,2N--CH2CH2 --NHCO), 2.78 (t,j=5.9 Hz,2H,N--CH2CH2 --NCS), 2.58 (t,j=6.4 Hz,4H, 2N--CH2CH2 --NHCO), 1.54 (s,12H,4CH3 --C--S) ppm. MS (m/z,CI): 633(25, MH+). IR (CDCl3): 3370, 2950, 2920, 2850, 2100, 1720, 1655, 1610, 1510, 1245, 1170, 1030, 830 cm-1.

Provenance & Evidence