Dimethyl Sulfoxide → HCID 178437191, compound

Temperature

-78 °C

To oxalyl chloride (0.85 μl, 0.976 mmol) in 5 ml of anhydrous dichloromethane at −78° C., dimethylsulfoxide (0.14 ml, 1.95 mmol) was added over a five minute period. After stirring for 5 minutes at the same temperature, 4-[1-(4,5-Dihydro-1H-imidazol-4-yl)-ethyl]quinoline (0.200 g, 0.888 mmol) was added slowly and the reaction mixture was stirred for a further 20 minutes at −78° C. Triethylamine (0.62 ml, 4.44 mmol) was added and the reaction mixture was stirred for 5 minutes at −78° C. and then 20 minutes at room temperature. The reaction mixture was concentrated under reduced pressure and partitioned between EtOAc (10 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and column purified [EtOAc:MeOH:Methanol NH3 (1.0 M); 3.5:1:0.5) to give 0.100 g (51%) of the product as a syrup.

1. additionwas added slowly
2. stirringthe reaction mixture was stirred for 5 minutes at −78° C.
3. custom20 minutes
4. customat room temperature
5. concentrationThe reaction mixture was concentrated under reduced pressure
6. custompartitioned between EtOAc (10 ml) and water (5 ml)
7. dry with materialThe organic layer was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customcolumn purified [EtOAc

ORD record

ord-3f977a45e6be452f8753489bf11fb0fc

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06294566B1