Diethyl Malonate → N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid ethyl ester

HRID 730474Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[S:13]([NH2:16])(=[O:15])=[O:14].[C:17](OCC)(=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[CH:4][C:3]=1[S:13](=[O:14])(=[O:15])[NH2:16])=[O:24])[CH3:23]

Participants

Reactant 2

HCID 7761Diethyl Malonate

HCID 249506572-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

Product 1

HCID 24858398N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid ethyl ester

Procedure

2-Amino-5-methanesulfonylamino-benzenesulfonamide (prepared as described in schemes 4 and 12) can be treated with a dialkyl malonate, such as diethyl malonate, to afford the desired N-(4-methanesulfonylamino-2-sulfamoyl-phenyl)-malonamic acid ethyl ester intermediate.

Sources & evidence

ORD record: ord-a21c47546fed44698326ca59a12a5098
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582754B2

Reaction notes

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