Toluene → HCID 86670499, compound

HRID 2188486Notes

Reaction equation

HRID 2188486 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.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:12]1([S:18]([N:21]=[C:8]=[C:7]2[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH2:6]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7370BenzenesulfonamideHCID 120884-Formylbenzoic acid

Product 1

HCID 86670499HCID 86670499, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An equimolar mixture of 25.0 g (0.17 mol) 4-carboxybenzaldehyde and 26.7 g (0.17 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. After cooling to room temperature, the precipitated solid was filtered off and dried under vacuum. Yield: 45.7 g (94.8%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=7.59 (m, 2H); 7.78 (d, 1H); 8.02 (m, 2H); 8.12 (d, 2H); 8.18 (d, 2H); 9.30 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=127.8; 129.7; 131.4; 134.1; 135.8; 136.0; 137.9; 166.5; 171.2; 192.9.

Workup

  1. temperatureThe mixture was then heated
  2. customhad separated
  3. filtrationthe precipitated solid was filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e1d4d7bf453541dc8fcc959b068e1d90
Source dataset
uspto-grants-2012_12
Patent number
US08323356B2

Reaction notes

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