Hydrazine hydrate (1:1) → 5-bromo-2-(hydrazinecarbonyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595598Notes

Reaction equation

HRID 595598 reaction equation
[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10](OC)=[O:11])=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[C:6]=2[CH:18]=1.O.[NH2:26][NH2:27]>CCO>[Br:1][C:2]1[C:3]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:26][NH2:27])=[O:11])=[C:7]([C:14]([NH:15][CH3:16])=[O:17])[C:6]=2[CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90332412methyl 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylate

Product 1

HCID 903325365-bromo-2-(hydrazinecarbonyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of compound methyl 5-bromo-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-2-carboxylate in EtOH was added hydrazine hydrate (421 mg, 7.16 mmol). The mixture was refluxed overnight. Then it was concentrated in vacuo and the resulting solid was washed with MeCN to give the compound 5-bromo-2-(hydrazinecarbonyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (600 mg, yield: 100%). It was used for the next step without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 10.33 (br s, 1H), 8.60 (s, 1H), 7.96 (s, 1H), 5.03 (br s, 3H), 3.22 (s, 3H), 3.20 (s, 3H), 2.87 (d, J=4.8 Hz, 3H). MS (M+H)+: 419/421.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThen it was concentrated in vacuo
  3. washthe resulting solid was washed with MeCN

Sources & evidence

ORD record
ord-38b549d7f52b41bb9e3be9b47709e5ce
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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