Hydrazine → 3-(Morpholine-4-sulfonyl)benzohydrazide

HRID 1777015

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13](OC)=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1.[NH2:20][NH2:21]>CO>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([NH:20][NH2:21])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl 3-(morpholinosulfonyl)benzoate (120 mg, 0.421 mmol) was added to hydrazine (17.52 mg, 0.547 mmol) in methanol and refluxed for 12 h at 65° C. The reaction was monitored by TLC. Upon completion of the reaction and cooling the reaction mixture, the solvent was removed by vacuum and then compound was purified by column chromatography to yield the title compound as an off white solid (90 mg). 1H NMR (400 MHz, CDCl3): δ 8.16 (m, 1H), 8.12 (m, 1H), 8.04 (m, 1H), 7.85 (m, 1H), 7.63 (t, 1H, J=8.0 Hz), 4.19 (m, 2H), 3.71 (m, 4H), 2.97 (m, 4H). ESI-MS: 286.1 [M+H]+.

Workup

customUpon completion of the reaction
temperaturecooling the reaction mixture
customthe solvent was removed by vacuum
customcompound was purified by column chromatography

Sources & evidence

ORD record: ord-d13c493a79f245d6bfe9765152d75767
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266838B2

Linked notes

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