Methyl iodide → HCID 5282538, compound

Reaction equation

[O-]CC.[Na+].[C:5]([NH:8][C:9](=[O:36])[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11]1[S:12][C:13]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)=[CH:14][C:15]=1[C:16]([O:18]CC)=O)(=O)C.IC>C(O)C>[CH3:5][N:8]1[C:16](=[O:18])[C:15]2[CH:14]=[C:13]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[S:12][C:11]=2[N:10]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:9]1=[O:36]

Participants

Procedure

Sodium ethoxide (0.18 g) was added to a stirred solution of N′-acetyl-N-(2-methylpropyl)-N-[3-ethoxycarbonyl-5-(1-naphthalenylmethyl)-2-thienyl]urea (Example 3, step c), 0.30 g) in ethanol (6 ml). After 6 hours, iodomethane (0.165 ml) was added. After a further 16 hours iodomethane (0.165 ml) was added, After a further 24 hours, the reaction mixture was poured onto hydrochloric acid (2M, 30 ml) and extracted with ethyl acetate (2×30 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ether:hexane (1:1) and then triturated with ether to give the title compound (0.24 g).