P-Toluenesulfonylhydrazide → 4-(4-Carboxyphenyl)-1-[2-methoxy-3-(4-methylphenyl)benzylidene]-3-thiosemicarbazide

HRID 1294728Notes

Reaction equation

HRID 1294728 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[S:14])[NH:12][NH2:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].[CH3:15][O:16][C:17]1[C:24]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O.S(NN)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[S:14])[NH:12][N:13]=[CH:19][C:18]2[CH:21]=[CH:22][CH:23]=[C:24]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[C:17]=2[O:16][CH3:15])=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazideHCID 225667032-Methoxy-3-(4-methylphenyl)benzaldehyde

Product 1

HCID 865915014-(4-Carboxyphenyl)-1-[2-methoxy-3-(4-methylphenyl)benzylidene]-3-thiosemicarbazideYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-carboxyphenyl)-3-thiosemicarbazide (11 mg, 0.05 mmol) and 2-methoxy-3-(4-methylphenyl)benzaldehyde (14 mg, 0.06 mmol) in dimethylformamide (1 mL) was shaken with 4 Å molecular sieves for 40 h. PS-TsNHNH2 resin (17 mg, 0.05 mmol) was added and shaking continued for 24 h, then the resin was filtered off. The solvent was removed under vacuum and the residue chromatographed by reverse phase HPLC (CombiPrep ODS-A, 10–90% acetonitrile/water+0.1% trifluoroacetic acid) to give the title compound (3 mg, 14%) as a solid. MS (ES−) m/e 418 [M−H]−.

Workup

  1. filtrationthe resin was filtered off
  2. customThe solvent was removed under vacuum
  3. customthe residue chromatographed by reverse phase HPLC (CombiPrep ODS-A, 10–90% acetonitrile/water+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-fc0359c5821e46069c85985ba538fb6c
Source dataset
uspto-grants-2007_07
Patent number
US07241783B2

Reaction notes

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