p-Toluenesulfonic acid → HCID 54199306, compound

HRID 2248539Notes

Reaction equation

HRID 2248539 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:19][S:16]([C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][CH:14]=2)(=[O:18])=[O:17])[CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 103713-PyridinecarboxaldehydeHCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 54199306HCID 54199306, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a similar manner to Example 2, 18.5 mmol of 3-pyridinecarboxaldehyde, 18.5 mmol of 4-chlorobenzenesulfonamide and 20 mg of TsOH in 100 mL of toluene reacted under reflux conditions to afford SULF-12 in 65% yield and high purity: 1H NMR (DSMO-d6, TMS ext std) δ9.3 (s,1), 9.2 (d, 1), 8.9 (m, 1), 8.4 (m, 1), 8.0-7.8 (AB. 4).

Workup

  1. customto afford SULF-12 in 65% yield and high purity

Sources & evidence

ORD record
ord-4f34dd3636664fb494a30e0db83d2582
Source dataset
uspto-grants-1991_08
Patent number
US05041232

Reaction notes

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