Chlorosulfonic acid → HCID 20201777, compound

HRID 979200Notes

Reaction equation

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

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 14468440HCID 14468440, compound

Product 1

HCID 20201777HCID 20201777, compoundYield 24%

Procedure

There was reacted 1.0 g (5.8 mmole) of 2-acetyl-7-methylbenzofuran with chlorosulfonic acid as in Example 1, yielding 0.36 g of 2-acetyl-4-chlorosulfonyl-7-methylbenzofuran (yield: 24%, MS (m/z): 232 (M+), 257, 237 and 173). The obtained chlorosulfonyl compound was reacted with glycine ethyl ester hydrochloride as in Example 1 to give an ester compound (yield: 73%, MS (m/z): 339 (M+), 266, 237 and 173), which was then hydrolyzed to give 2-acetyl-4-(N-carboxymethylsulfamoyl)-7-methylbenzofuran (yellow plates, yield: 71%). The physical constants are shown in Table 4.

Sources & evidence

ORD record: ord-84c80c536bdc494e952337dceda5cb29
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04666931

Reaction notes

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