N-Iodosuccinimide → HCID 59208395, compound

Reaction equation

IN1C(=O)CCC1=O.[CH3:9][O:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18](=O)[CH2:19][C:20]([O:22][CH3:23])=[O:21].[NH2:25][C:26]([NH2:28])=[S:27]>CCOC(C)=O>[NH2:28][C:26]1[S:27][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([C:14]2[N:13]([CH2:12][CH2:11][O:10][CH3:9])[CH:17]=[CH:16][N:15]=2)[N:25]=1

Participants

Procedure

N-Iodosuccinimide (9.3 g, 41 mmol) was added to a mixture of 7.52 g (41 mmol) methyl 3-[1-(2-methoxyethyl)-1H-imidazol-2-yl]-3-oxopropanoate (Intermediate 56) and 7.5 g Amberlyst-15 resin in 400 ml EtOAc followed by stirring for 1 hour at room temperature. The resin was filtered off and rinsed with EtOAc. Solvent was removed from the filtrate and the residue was taken up in diethyl ether. Insoluble material was filtered off and rinsed with additional ether. Solvent was removed from the filtrate and the residue was dissolved in 200 ml MeOH before added 4.7 g (62 mmol) thiourea. The mixture was heated at reflux for 1 hour. Then the solvent was removed and the residue was taken up in aqueous Na2CO3. Insoluble material was collected by filtration and rinsed well with water. The solids were dried in vacuo affording 4.51 g of the title compound: MS (ES) (M+H)+: 283 for C11H14N4O3S; NMR: 3.22 (s, 3H), 3.61 (m, 2H), 3.69 (s, 3H), 4.32 (m, 2H), 7.91 (s, 2H), 8.41 (s, 2H).