HCID 59021684, compound → HCID 11626867, compound

HRID 971311Notes

Reaction equation

HRID 971311 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[CH2:14][C:15]([NH:17]/[N:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-])=O)=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH3:2]>C(Cl)Cl.[Pd]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1/[CH:19]=[N:18]/[NH:17][C:15](=[O:16])[CH2:14][N:13]([C:29]1[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=1)[S:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=1)(=[O:12])=[O:11]

Participants

4

Reactant 1

HCID 59021684HCID 59021684, compound

Product 1

HCID 11626867HCID 11626867, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

4-ethoxy-N-(4-methylphenyl)-N-{2-[(2E)-2-(2-nitrobenzylidene)hydrazino]-2-oxoethyl}benzenesulfonamide (99 mg, 0.2 mmol) was dissolved in methylene chloride. Palladium 5% on charcoal was added (10 mol %). The mixture was stirred under H2 at athmospheric pressure at room temperature overnight. It was filtered on Celite and solvents were evaporated. The expected product, e.g. N-{2-[(2E)-2-(2-aminobenzylidene)hydrazino]-2-oxoethyl}-4-ethoxy-N-(4-methylphenyl)benzenesulfonamide (71.2 mg, 76%), was obtained as a light yellow solid, in 90.9% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. filtrationIt was filtered on Celite and solvents
  2. customwere evaporated

Sources & evidence

ORD record
ord-a6cd8e2edeba40da906d6aa8c6cf71c1
Source dataset
uspto-grants-2007_12
Patent number
US07312358B2

Reaction notes

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