Aluminium lithium hydride → 1-(3,4-Dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea

Participants

Reaction Steps

1.0 g of 2-(3-(3,4-dichlorobenzyl)ureido)-N-methoxy-N-methylthiazole-4-carboxamide was dissolved in 20 ml dry tetrahydrofuran and cooled to −78 C. 1.10 eq. of 1 N lithium aluminum hydride in tetrahydrofuran was added slowly. The reaction was stirred at 0 C for 2 hours. The reaction was cooled to −78 C again and quenched with 1 N HCl and extracted with EtOAc three times. The organic was combined, dried over sodium sulfate and concentrated. The residue was purified by column chromatography using 0-100% gradient of EtOAc and hexanes to give 1-(3,4-dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea.

Provenance & Evidence