Toluene → 4-{[(4-Chlorobenzene-1-sulfonyl)imino]methyl}benzoic acid

HRID 2188488Notes

Reaction equation

HRID 2188488 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].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([N:22]=[CH:8][C:7]2[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)(=[O:20])=[O:21])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 120884-Formylbenzoic acidHCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 542634144-{[(4-Chlorobenzene-1-sulfonyl)imino]methyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An equimolar mixture of 25.0 g (0.17 mol) 4-carboxybenzaldehyde and 32.6 g (0.17 mol) 4-chlorobenzenesulfonamide 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: 48.3 g (89.4%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=7.78 (d, 2H); 8.09 (d, 2H); 8.11 (d, 2H); 8.23 (d, 2H); 9.29 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=130.2; 130.5; 131.8; 135.5; 136.0; 136.1; 139.1; 166.6; 171.9; 193.0.

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-9e99c24c32bd416f8606c99061275eb3
Source dataset
uspto-grants-2012_12
Patent number
US08323356B2

Reaction notes

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