2-Aminobenzenesulfonamide → 2-Amino-5-iodobenzenesulfonamide

HRID 884196Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[I:12]N1C(=O)CCC1=O>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:12])=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10]

Participants

Reactant 2

HCID 728942-Aminobenzenesulfonamide

HCID 120273N-Iodosuccinimide

Product 1

HCID 223240882-Amino-5-iodobenzenesulfonamide

Procedure

Commercially available 2-aminobenzenesulfonamide can be treated with N-iodosuccinimide (NIS) to afford 2-amino-5-iodo-benzenesulfonamide. Acylation with a malonyl halide monoester, such as ethyl 3-chloro-3-oxo-propionate, or with a dialkyl malonate, such as diethyl malonate, affords the corresponding amide, which can simultaneously be cyclized to the thiadiazine-dioxide and hydrolyzed to the desired acid intermediate (or a salt thereof, e.g., sodium salt).

Sources & evidence

ORD record: ord-fc804453b2ba45eda65a523f27721e73
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236948B2

Reaction notes

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