[Na].[OH:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13].Cl.[CH3:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH2:21]Cl>C(O)C>[CH3:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH2:21][O:2][N:3]1[C:4](=[O:13])[C:5]2=[CH:12][CH:11]=[CH:10][CH:9]=[C:6]2[C:7]1=[O:8]A mixture of 1 g of sodium and 80 ml of ethanol was cooled in an ice-bath and 7.12 g of N-hydroxyphthalimide was added thereto and the mixture was stirred at room temperature. The mixture was cooled in an ice-bath and 3.16 g of 5-methyl-4-chloromethylimidazole hydrochloride was added thereto. The resulting mixture was stirred for 2 hours. The solvent was distilled off and SSB was added to the residue and the mixture was extracted with chloroform. The extract was washed with SSC and dried with sodium sulfate and concentrated to dryness. The residue was washed with ether to give 2.37 g of N-((5-methylimidazole-4-yl)methoxy)phthalimide with mp 155°-156° C.
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