Ethanol → 2-(4-Methyl-2,5-dioxoimidazolidine-4-yl)-7-methoxybenzofuran

HRID 979203Notes

Reaction equation

HRID 979203 reaction equation
C([C:4]1[O:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=O)C.[C:15](=[O:18])([O-])[O-].[NH4+:19].[NH4+:20].[C-:21]#N.[Na+].[CH2:24]([OH:26])[CH3:25]>>[CH3:21][C:25]1([C:4]2[O:5][C:6]3[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=3[CH:8]=2)[C:24](=[O:26])[NH:20][C:15](=[O:18])[NH:19]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 39378Ethanone, 1-(7-methoxy-2-benzofuranyl)-HCID 517111Ammonium Carbonate

Product 1

HCID 144684512-(4-Methyl-2,5-dioxoimidazolidine-4-yl)-7-methoxybenzofuranYield 45%

Procedure

2-Acetyl-7-methoxybenzofuran was reacted with ammonium carbonate and sodium cyanide in 60% ethanol to give 2-(4-methyl-2,5-dioxoimidazolidine-4-yl)-7-methoxybenzofuran (yield: 45%, MS (m/z): 260 (M+), 245, 189 and 174), which was then reacted with chlorosulfonic acid as in Example 1, yielding 2-(4-methyl-2,5-dioxoimidazolidine-2-yl)-4,6-dichlorosulfonyl-7-methoxybenzofuran (yield: 83%, MS (m/z): 456 (M+), 421, 385 and 350). The obtained product was reacted with glycine-t-butyl ester hydrochloride as in Example 19 to give a di-t-butyl ester compound (yield: 90%), which was treated with trifluoroacetic acid as in Example 19 to give 2-(4-methyl-2,5-dioxoimidazolidine-4-yl)-4,6-di(N-carboxymethylsulfamoyl)-7-methoxybenzofuran (colorless amorphous powder, yield: 97%). The physical constants are shown in Table 4.

Sources & evidence

ORD record
ord-31e7615bfc7d4ab1a90028a226335cf0
Source dataset
uspto-grants-1987_05
Patent number
US04666931

Reaction notes

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