Aluminium lithium hydride → 1-(3,4-Dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][NH:6][C:7](=[O:20])[NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](N(OC)C)=[O:15])[N:13]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:5][NH:6][C:7]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH:14]=[O:15])[N:13]=1)=[O:20]Participants
4
Procedure
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.