Chlorosuccinimide → 5-bromo-N-hydroxy-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carbimidoyl chloride

HRID 595667Notes

Reaction equation

[Br:1][C:2]1[C:3]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:4][C:5]2[O:9][C:8]([CH:10]=[N:11][OH:12])=[C:7]([C:13]([NH:15][CH3:16])=[O:14])[C:6]=2[CH:17]=1.C1C(=O)N([Cl:31])C(=O)C1>CN(C=O)C>[Br:1][C:2]1[C:3]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:20])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]([Cl:31])=[N:11][OH:12])=[C:7]([C:13](=[O:14])[NH:15][CH3:16])[C:6]=2[CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5-bromo-2-((hydroxyimino)methyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.25 mmol) and NCS (40 mg, 0.30 mmol) in DMF (2 mL) was stirred at 60° C. for 18 h. The mixture was used for the next step without purification, 5-bromo-N-hydroxy-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carbimidoyl chloride was obtained (90 mg, yield: 65%). 1H-NMR (DMSO-d6, 400 MHz) δ 13.33 (s, 1H), 8.65 (d, J=4 Hz, 1H), 8.13 (s, 1H), 8.05 (s, 1H), 3.20 (s, 6H), 2.80 (d, J=4.8 Hz, 3H). MS (M+H)+: 438/440.

Workup

customThe mixture was used for the next step without purification

Sources & evidence

ORD record: ord-37474506c0ab44bda6c90c1f1238053c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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