Chlorosulfonic acid → HCID 20201791, compound

HRID 979199Notes

Reaction equation

[C:1]([C:3]1[O:4][C:5]2[C:11]([O:12][CH2:13][CH3:14])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)#[N:2].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[C:1]([C:3]1[O:4][C:5]2[C:11]([O:12][CH2:13][CH3:14])=[CH:10][CH:9]=[C:8]([S:16]([Cl:15])(=[O:18])=[O:17])[C:6]=2[CH:7]=1)#[N:2]

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 14468445HCID 14468445, compound

Product 1

HCID 20201791HCID 20201791, compoundYield 43%

Procedure

There was reacted 1 g (5.4 mmole) of 2-cyano-7-ethoxybenzofuran (with chlorosulfonic acid as in Example 1, yielding 0.65 g of 2-cyano-4-chlorosulfonyl-7-ethoxybenzofuran (yield: 43%, MS (m/z): 285 (M+), 257, 250 and 222). The obtained chlorosulfonyl compound was reacted with glycine ethyl ester hydrochloride as in Example 1 to give an ester compound (yield: 46%, MS (m/z): 385 (M+), 279, 250 and 222), which was then hydrolyzed, accompanying the hydrolysis of nitrile, to give 2-carboxy-4-(N-carboxymethylsulfamoyl)-7-ethoxybenzofuran (yellow prisms, yield: 62%). The physical constants are shown in Table 4.

Sources & evidence

ORD record: ord-4ea861f5107b45f38e538b9b6ef1ec51
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04666931

Reaction notes

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