Water → HCID 54354143, compound

HRID 888305Notes

Reaction equation

[NH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[C:5]([CH2:13][OH:14])[CH:4]=1)[NH2:2].C(N(CC)CC)C.[CH:22]1([C:28](=O)[CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.O>C(O)C>[CH:32]1([C:30]2[CH:29]=[C:28]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:1]([C:3]3[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:10])=[O:11])=[C:5]([CH2:13][OH:14])[CH:4]=3)[N:2]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-hydrazinyl-2-(hydroxymethyl)benzenesulfonamide (224 mg, 0.884 mmol) in ethanol (4.0 mL), triethylamine (246 μL, 1.77 mmol) and 1-cyclohexyl-3-phenylpropan-1,3-dione (185 mg, 0.803 mmol) were added, and the obtained solution was stirred at 100° C. for 72 hours. Water was added to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/chloroform/acetone) to obtain the title compound (51.5 mg, 0.125 mmol, 16%) as a white amorphous product.

Workup

additionwere added
extractionthe resulting solution was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (silica gel, n-hexane/chloroform/acetone)

Sources & evidence

ORD record: ord-07bf0febc9aa42b88aaf57455e115d34
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247569B2

Reaction notes

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