4-(hydrazinocarbonyl)-N-methylbenzenesulfonamide → 4-({2-[[5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl](phenyl)methylene]hydrazino}carbonyl)-N-methylbenzenesulfonamide

HRID 2103872Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=O)[C:12]=2[OH:25])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:26]([C:28]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:39][CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=1)=[O:29])[NH2:27]>C(O)(C)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:27][NH:26][C:28]([C:30]3[CH:31]=[CH:32][C:33]([S:36]([NH:39][CH3:40])(=[O:37])=[O:38])=[CH:34][CH:35]=3)=[O:29])[C:12]=2[OH:25])=[CH:9][CH:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

[5-(4-t-Butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl] (phenyl)methanone (0.254 mmol, 85 mg), 4-(hydrazinocarbonyl)-N-methylbenzenesulfonamide (0.254 mmol, 58 mg) and p-tosylic acid monohydrate (30 mol %, 13 mg) were dissolved in isopropyl alcohol (8.5 mL) and stirred at 100° C. for 19 hours. Then, the solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform/methanol=10/1) to give the desired product as a yellow solid (30.3 mg, yield 22%).

Workup

customThen, the solvent was evaporated
customthe residue was purified by silica gel thin layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record: ord-59d181443d5c46c68677439ffb26da26
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576115B2

Reaction notes

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