Aluminum(III) Chloride → HCID 2752457, compound
Reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH2:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClC(Cl)C(Cl)Cl>[S:16]=[C:15]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:11][C:12](=[O:13])[NH:14]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 250 mL round bottom flask was added anhydrous aluminum chloride powder (21.6 g, 162.2 mmol) and 1,1,2,2-tetrachloroethane (20 mL). The resulting solution was cooled to 0° C. under Ar and then a solution of phenylacetyl isothiocyanate (12.5 g, 70.5 mmol) in 1,1,2,2-tetrachloroethane (10 mL) was added dropwise via addition funnel over a period of 10 min. Upon completion of addition, the reaction mixture was stirred at 95° C. for 1 h during which time the slurry became a dark brown solution. The reaction mixture was then allowed to cool to RT. Once at the prescribed temperature, the reaction mixture was carefully quenched with a solution of cold HCl (250 mL, 2.4 N). The resultant beige precipitate was collected by vacuum filtration, air dried for 0.5 h and then recrystallized from glacial AcOH and decolorizing charcoal to yield the title compound as an orange crystalline solid (7.2 g, 40.6 mmol, 58%). 1H NMR (400 MHz, CDCl3): δ ppm 3.29 (s, 1H), 11.78 (s, 1H), 8.57 (d, 1H, J=8.35 Hz), 7.59-LC/MS m/z [M+H].
Workup
- additionUpon completion of addition
- temperatureto cool to RT
- customOnce at the prescribed temperature, the reaction mixture was carefully quenched with a solution of cold HCl (250 mL, 2.4 N)
- filtrationThe resultant beige precipitate was collected by vacuum filtration, air
- customdried for 0.5 h
- customrecrystallized from glacial AcOH
Sources & evidence
- ORD record
- ord-9d3182fc01f04392b1d9aeecc7fd06dc
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318941B2
Reaction notes
Loading…