Chlorodimethylaluminum → N-(4-Methoxybenzyl)thiazol-4-amine

To a solution of tert-butyl 4-methoxybenzyl(thiazol-4-yl)carbamate (20.0 g, 62.4 mmol) in THF (100 mL) was added Me2AlCl (1M in THF, Aldrich) (93.6 mL, 93.6 mmol) at 0° C. The reaction was allowed to stir at room temperature for 5 h. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate (2×500 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude material which was further purified by column chromatography (silica gel 100-200 mesh and 0-50% ethyl acetate in hexanes) to obtain N-(4-methoxybenzyl)thiazol-4-amine (9.8 g, 73%) as an off-white solid. MS (ESI, positive ion) m/z=220.9 (M+1)+. 1H NMR (400 MHz, DMSO) δ 8.73 (d, J=2.2 Hz, 1H), 7.28 (d, J=8.5 Hz, 2H), 6.96-6.76 (m, 2H), 6.54 (t, J=6.3 Hz, 1H), 5.76 (d, J=2.2 Hz, 1H), 4.18 (d, J=6.2 Hz, 2H), 3.71 (s, 3H).

1. additionThe reaction mixture was poured into ice-cold water
2. extractionextracted with ethyl acetate (2×500 mL)
3. dry with materialThe combined organic layer was dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customto obtain the crude material which
7. customwas further purified by column chromatography (silica gel 100-200 mesh and 0-50% ethyl acetate in hexanes)

ORD record

ord-40e8a32c4b6640b589f69a7eaffff9ce

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012443B2