p-Toluenesulfonic acid → HCID 137178920, compound

HRID 1357456Notes

Reaction equation

HRID 1357456 reaction equation
[CH:1]([C:3]1[C:4]([OH:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.C1(C)C=CC(C2C(C([NH:28][NH2:29])=O)=CC=CC=2)=CC=1.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34](S(O)(=O)=O)=[CH:33][CH:32]=1>CO>[OH:13][C:4]1[C:3]([CH:1]=[N:28][NH:29][C:34]2[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=2)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 345559methyl 3-formyl-2-hydroxybenzoateHCID 13937904'-Methylbiphenyl-2-carbohydrazide

Product 1

HCID 137178920HCID 137178920, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 1.1 g (6 mmol) of the aldehyde of Example 2 in 30 ml of anhydrous methanol was reacted with 0.9 g (6 mmol) of p-toluenebenzohydrazide with acid catalysis (para-toluenesulfonic acid). After the reaction mixture had been stirred for approximately 14 hours at 20 to 25° C., it was freed from the solvent. 1.9 g of the title compound, which corresponded to 99% of theory, were obtained from the residue. (m.p. 134-137° C.)

Sources & evidence

ORD record
ord-db4757e97d524b61a6d3ed714ffb9500
Source dataset
uspto-grants-2003_07
Patent number
US06593315B2

Reaction notes

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