Chloroacetyl chloride → HCID 18918637, compound

Temperature

5 °C

To an ice-cold solution of chloroacetyl chloride (2.87 g, 25 mmol) in 15 mL of methylene chloride was added thiomorpholine (2.50 g, 24 mmol) and triethylamine (4.9 g, 48 mmol) slowly. The reaction mixture was stirred at 5° C. for 30 minutes, then warmed to room temperature and stirred for 18 hours. After quenching with water (20 mL) at 5° C., additional methylene chloride (200 mL) was added. The organic layer was separated, washed with saturated aqueous NaHCO3 (2×100 mL), brine (2×100 mL), dried over MgSO4, filtered, and the filtrate was concentrated at reduced pressure. The concentrated residue was dried in vacuo to give 1.83 g (42.0%) of 4-(2-chloroacetyl) thiomorpholine as a brown liquid. 1HNMR (300 MHz / CDCl3):δ 2.62 (t, 2H, J=5.03 Hz), 2.68 (t, 2H, J=4.93Hz), 3.75 (t, 2H, J=5.04 Hz), 3.85 (t, 2H, J=5.04 Hz), 4.04 (s, 2H); mass spectrum, m/z =180.2 (M+H).

1. temperaturewarmed to room temperature
2. stirringstirred for 18 hours
3. customAfter quenching with water (20 mL) at 5° C.
4. additionadditional methylene chloride (200 mL) was added
5. customThe organic layer was separated
6. washwashed with saturated aqueous NaHCO3 (2×100 mL), brine (2×100 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthe filtrate was concentrated at reduced pressure
10. customThe concentrated residue was dried in vacuo

ORD record

ord-5755edda85214b96a38ca9113941c02c

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753660