Chlorosulfonic acid → 2-Methoxycarbonyl-4-chlorosulfonyl-7-methoxybenzofuran

HRID 979198Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:8]=2[CH:9]=1)=[O:4].[Cl:16][S:17](O)(=[O:19])=[O:18]>>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([S:17]([Cl:16])(=[O:19])=[O:18])[C:8]=2[CH:9]=1)=[O:4]

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 12269509Methyl 7-methoxy-1-benzofuran-2-carboxylate

Product 1

HCID 202017902-Methoxycarbonyl-4-chlorosulfonyl-7-methoxybenzofuranYield 80%

Procedure

There was reacted 1.7 g (8.25 mmole) of 2-methoxycarbonyl-7-methoxybenzofuran with chlorosulfonic acid as in Example 1, yielding 2 g of 2-methoxycarbonyl-4-chlorosulfonyl-7-methoxybenzofuran (yield: 80%, MS (m/z): 304 (M+), 269, 238 and 210). The obtained chlorosulfonyl compound was reacted wit glycine ethyl ester hydrochloride as in Example 1 to give an ester compound (yield: 88%, MS (m/z): 371 (M+), 340, 298 and 269), which was then hydrolyzed to give 2-carboxy-4-(N-carboxymethylsulfamoyl)-7-methoxybenzofuran (colorless needles, yield: 86%). The physical constants are shown in Table 4.

Sources & evidence

ORD record: ord-29063aa3600842bf9e61fb6ca9ef9ed1
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04666931

Reaction notes

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