Chlorosulfonic acid → 2-Acetyl-7-(butan-2-yl)-1-benzofuran-4-sulfonyl chloride
Reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[Cl:17][S:18](O)(=[O:20])=[O:19]>>[C:1]([C:4]1[O:5][C:6]2[C:12]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:11][CH:10]=[C:9]([S:18]([Cl:17])(=[O:20])=[O:19])[C:7]=2[CH:8]=1)(=[O:3])[CH3:2]Participants
3
Procedure
There was reacted 1 g (4.6 mmole) of 2-acetyl-7-sec-butylbenzofuran with chlorosulfonic acid as in Example 1, yielding 0.97 g of 2-acetyl-4-chlorosulfonyl-7-sec-butylbenzofuran (yield: 67%, MS (m/z): 314 (M+), 285 and 186). The obtained chlorosulfonyl compound was reacted with glycine ethyl ester hyrochloride as in Example 1 to give an ester compound (yield: 82%, MS (m/z): 381 (M+), 352, 308 and 279), which was then hydrolyzed to give 2-acetyl-4-(N-carboxymethylsulfamoyl)-7-sec-butylbenzofuran (light yellow plates, yield: 73%). The physical constants are shown in Table 4.
Sources & evidence
- ORD record
- ord-a9a329271c3e489ca36092d4d330de6b
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04666931
Reaction notes
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