p-Toluenesulfonic acid → 4-{[(Benzenesulfonyl)imino]methyl}benzoic acid

HRID 727990Notes

Reaction equation

HRID 727990 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:12]1([S:18]([NH2:21])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:21][S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7370BenzenesulfonamideHCID 120884-Formylbenzoic acid

Product 1

HCID 544334374-{[(Benzenesulfonyl)imino]methyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 2, 1.00 g (6.6 mmol) of 4-carboxybenzaldehyde, 1.05 g (6.6 mmol) of benzenesulfonamide and 20 mg of TsOH in 120 mL of toluene were heated for 2.5 hours to afford 1.82 g (90%) of SULF-2 as a white powder; IR (Nujol) 3400-2400 (br), 1680, 1605, 1283, 1160, 1083 cm-1 ; 1H NMR (DMSO-d6, TMS ext std)δ9 .17 (s, 1), 8.1-7.3 (m, 9).

Workup

  1. customto afford 1.82 g (90%) of SULF-2 as a white powder

Sources & evidence

ORD record
ord-f20e499fa7494cc7a8fd2c544a6e9974
Source dataset
uspto-grants-1991_09
Patent number
US05047163

Reaction notes

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