p-Toluenesulfonic acid → N-(4-Methoxybenzylidene)-4-carboxybenzenesulfonamide

HRID 2248537Notes

Reaction equation

HRID 2248537 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=O)=[CH:7][CH:8]=1.[C:11]([C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)([OH:13])=[O:12].CC1C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[N:23][S:20]([C:17]2[CH:16]=[CH:15][C:14]([C:11]([OH:13])=[O:12])=[CH:19][CH:18]=2)(=[O:21])=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8739CarzenideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 53646612N-(4-Methoxybenzylidene)-4-carboxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a similar manner to Example 2, 1.28 g (9 mmol) of anisaldehyde, 1.89 g (9 mmol) of 4-carboxybenzenesulfonamide and 20 mg of TsOH in 150 mL of chlorobenzene and under nitrogen were heated for 4.5 hours to yield 2.86 g (96%) of SULF-8 as a white powder: IR (Nujol) 3300-2700 (br), 1693, 1601, 1584, 1155 cm-1 ; 1H NMR (DMSO-d6, TMS ext std) δ8.91 (s, 1), 8.4-7.7 (m, 8), 3.92 (s, 3).

Workup

  1. customto yield 2.86 g (96%) of SULF-8 as a white powder

Sources & evidence

ORD record
ord-77293986840d4bc18128aae8a92c1ab6
Source dataset
uspto-grants-1991_08
Patent number
US05041232

Reaction notes

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