Pyridine → HCID 22236063, compound

Temperature

-78 °C

To a cold (−78° C.) solution of 5-amino-3-methylisothiazole hydrochloride (21.2 g, 127 mmol), pyridine (68 mL, 841 mmol) and DMAP (4.62 g, 38 mmol) in CH2Cl2 (420 mL) was slowly added trichloroethylchloroformate (31 mL, 224 mmol) over a period of 15 min. The reaction mixture was stirred at −78° C. for 30 min and then warmed to room temperature for 1 h. The mixture was partitioned between EtOAc and water, the organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was disolved in Et2O (800 mL), charcoal was added and the resulting black suspension was boiled for 15 min and allowed to stand at room temperature for 18 h. The charcoal was removed by filtration on a pad of celite and the filtrate was concentrated in vacuo. The crude product was crystallized from a hot mixture of Et2O/hexane (1:1, 600 mL) to yield 2,2,2-trichloroethyl 3-methylisothiazol-5-ylcarbamate as a light yellow solid.

1. customof 15 min
2. temperaturewarmed to room temperature for 1 h
3. customThe mixture was partitioned between EtOAc and water
4. dry with materialthe organic layer was dried over MgSO4
5. concentrationconcentrated in vacuo
6. additioncharcoal was added
7. waitthe resulting black suspension was boiled for 15 min
8. waitto stand at room temperature for 18 h
9. customThe charcoal was removed by filtration on a pad of celite
10. concentrationthe filtrate was concentrated in vacuo
11. customThe crude product was crystallized from a hot mixture of Et2O/hexane (1:1, 600 mL)

ORD record

ord-6ad24334b331459ba38ac2f7d526b185

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012075B2