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

HRID 2211315

Reaction equation

HRID 2211315 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1)([OH:12])=[O:11].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:22][S:19]([C:16]2[CH:17]=[CH:18][C:13]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 77264-ChlorobenzaldehydeHCID 8739Carzenide

Product 1

HCID 54557984N-(4-Chlorobenzylidene)-4-carboxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar manner to Example 2, 4.00 g (29 mmol) of 4-chlorobenzaldehyde, 5.72 g (29 mmol) of 4-carboxybenzenesulfonamide and 20 mg of TsOH in 150 mL of toluene were heated for 24 hours to provide 6.60 g (71%) of SULF-3 as a light tan powder: IR (Nujol) 3400-2500 (br), 1685, 1595, 1285, 1215, 1005 cm-1 ; 1H NMR (DMSO-d6, TMS ext std) δ 9.15 (s, 1), 8.2-7.3 (m, 8).

Workup

  1. customto provide 6.60 g (71%) of SULF-3 as a light tan powder

Sources & evidence

ORD record
ord-ec5ac22661054136a0935775a4b368c7
Source dataset
uspto-grants-1995_10
Patent number
US05463115

Linked notes

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