Chlorodimethylaluminum → N-[(4-methoxyphenyl)methyl]-1,3-thiazol-4-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]([C:16]2[N:17]=[CH:18][S:19][CH:20]=2)C(=O)OC(C)(C)C)=[CH:5][CH:4]=1.[Al](Cl)(C)C>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:16]2[N:17]=[CH:18][S:19][CH:20]=2)=[CH:21][CH:22]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).