Toluene → HCID 2759534, compound

HRID 2188487Notes

Reaction equation

HRID 2188487 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]1([S:17]([NH2:20])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:20][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7370BenzenesulfonamideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 2759534HCID 2759534, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An equimolar mixture of 25.0 g (0.18 mol) 4-methoxybenzaldehyde and 28.3 g (0.18 mol) benzenesulfonamide was placed into toluene. 100 mg p-toluenesulfonic acid was added as a catalyst. The mixture was then heated under reflux on a water separator until the theoretically calculated quantity of water had separated. The reaction mixture was cooled first to room temperature and then in a refrigerator to 10° C. The precipitated solid was then filtered off and dried under vacuum. Yield: 37.6 g (74.3%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=7.13 (d, 2H); 7.69 (m, 2H); 7.77 (d, 1H); 7.96 (d, 2H); 8.04 (d, 2H); 9.11 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=55.6; 114.7; 124.9; 127.5; 129.6; 133.8; 134.0; 138.8; 165.0; 170.8.

Workup

  1. temperatureThe mixture was then heated
  2. customhad separated
  3. customto 10° C
  4. filtrationThe precipitated solid was then filtered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-aa52cdeb098e40c7844bd25c35ca880d
Source dataset
uspto-grants-2012_12
Patent number
US08323356B2

Reaction notes

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