Benzenesulfonyl hydrazide → Methyl 4-(4-oxo-chroman-3-ylmethyl)-benzoate

HRID 252764

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][C:3]1=[CH:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.C1(S(NN)(=O)=O)C=CC=CC=1>CN(C=O)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 260 (400 mg, 1.36 mmol) and benzenesulfonyl hydrazine (702 mg, 4.08 mmol) in DMF (7 ml) was stirred at 100° C. during 48 h. The solvent was evaporated and the residue was diluted in AcOEt, washed with NH4Cl sat., brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (5% AcOEt/HEx) to afford the title compound 264 (170 mg, 42%) as a white solid. LRMS: 296.1 (Calc.); 297.0 (found).

Workup

customThe solvent was evaporated
additionthe residue was diluted in AcOEt
washwashed with NH4Cl sat., brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was then purified by flash chromatography on silica gel (5% AcOEt/HEx)

Sources & evidence

ORD record: ord-ac08051bbd874a95ae102b7fbb1a3e70
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868204B2

Linked notes

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