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

HRID 727989Notes

Reaction equation

HRID 727989 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(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[N:22][S:19]([C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=2)(=[O:21])=[O:20])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 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 1140TolueneSolvent

Procedure

A well-stirred slurry consisting of 4.64g (31 mmol) of 4-carboxybenzaldehyde and 5.92 g (31 mmol) of 4-chlorobenzenesulfonamide and 20 mg of p-toluenesulfonic acid (TsOH) in 130 mL of toluene was heated to reflux for a total of 5 hours. The water formed from the reaction was removed by a Soxhlet extractor packed with 3A molecular sieves as described above. The mixture was allowed to cool to room temperature and was filtered to provide 9.76 g (98%) of SULF-1 as a white powder: mp >245° C.; IR (Nujol) 3300-2300 (br), 3090, 1689, 1616, 1168, 1013 cm-1 ; 1H NMR (DSMO-d6, TMS ext standard, 60 MHz) δ9.15 (s, 1), 8.01 (s, 4), 7.79 (AB, 4, JAB =11, Δν=16).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for a total of 5 hours
  3. customwas removed by a Soxhlet extractor
  4. filtrationwas filtered
  5. customto provide 9.76 g (98%) of SULF-1 as a white powder

Sources & evidence

ORD record
ord-864a472466b04c3ea1d6cb58625e0e66
Source dataset
uspto-grants-1991_09
Patent number
US05047163

Reaction notes

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