Tert-Butanesulfinamide → 2-methyl-N-[(1E)-1,3-oxazol-4-ylmethylidene]propane-2-sulfinamide

In a round-bottomed flask, oxazole-4-carbaldehyde (300 mg, 3.09 mmol) was dissolved in THF (7 ml) and 2-methylpropane-2-sulfinamide (450 mg, 3.71 mmol) and titanium(IV) ethoxide (1.3 ml, 6.18 mmol) were added. The reaction mixture was stirred at room temperature overnight then slowly quenched by dropwise addition of brine (2 ml) which resulted in the formation of a thick light yellow precipitate. The reaction mixture was diluted with ethyl acetate and stirred vigorously at room temperature for 30 min. The suspension was filtered over Celite and rinsed with ethyl acetate. The filtrate was concentrated and the residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-40% EtOAc) to afford 552 mg (89%) of 2-methyl-propane-2-sulfinic acid 1-oxazol-4-yl-meth-(E)-ylideneamide as a white solid.

1. customthen slowly quenched by dropwise addition of brine (2 ml) which
2. customresulted in the formation of a thick light yellow precipitate
3. stirringstirred vigorously at room temperature for 30 min
4. filtrationThe suspension was filtered over Celite
5. washrinsed with ethyl acetate
6. concentrationThe filtrate was concentrated
7. customthe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-40% EtOAc)

ORD record

ord-9530f0ef6728462ebcaeec952ed721dc

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2