[CH2:1]([C:3]([NH:8][C:9]([NH:11]C(=O)C1C=CC=CC=1)=[S:10])([CH2:6][OH:7])[CH2:4][CH3:5])[CH3:2].[Li+].[OH-]>O1CCCC1.CO.O>[CH2:1]([C:3]([NH:8][C:9]([NH2:11])=[S:10])([CH2:6][OH:7])[CH2:4][CH3:5])[CH3:2]A solution of N-({[1-ethyl-1-(hydroxymethyl)propyl]amino}carbonothioyl)benzamide (6.8779 g, 24.5 mmol), prepared in the previous step, and 1 M LiOH (29.4 mL, 29.4 mmol) in 200 mL of tetrahydrofuran plus 200 mL of methanol plus 100 mL of water was stirred under nitrogen at room temperature for 21 h. The reaction was concentrated under reduced pressure to remove most of the tetrahydrofuran and methanol. The solid present was collected by filtration and dried under reduced pressure to give N-[1-ethyl-1-(hydroxymethyl)propyl]thiourea (2.9228 g, 68%) as a white solid, mp 148-151° C.; MS (ESI) m/z 177 [M+H]+.
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