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

HRID 2182469Notes

Reaction equation

HRID 2182469 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

4

Reactant 2

HCID 65723Benzenesulfonyl hydrazideHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

Product 1

HCID 22478914Methyl 4-(4-oxo-chroman-3-ylmethyl)-benzoateYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

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

Sources & evidence

ORD record
ord-133fdb3f2e8f4048b1c46df5cb0d2204
Source dataset
uspto-grants-2005_05
Patent number
US06897220B2

Reaction notes

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