p-Toluenesulfonic acid → HCID 87057700, compound

HRID 1529044Notes

Reaction equation

HRID 1529044 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[CH3:16][S:17]([NH2:20])(=[O:19])=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2/[CH:14]=[N:20]/[S:17]([CH3:16])(=[O:19])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 72879MethanesulfonamideHCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde

Product 1

HCID 87057700HCID 87057700, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (2 g, 7.5 mmol), methane sulfonamide (0.714 g, 7.5 mmol) and p-toluenesulfonic acid (0.010 g, 0.06 mmol) were combined in toluene. The reaction was heated to reflux for 24 hours with Dean-Stark apparatus in place. Upon cooling, the title compound precipitated from solution and was collected by filtration and used directly in the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 24 hours with Dean-Stark apparatus in place
  3. temperatureUpon cooling
  4. customthe title compound precipitated from solution
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c9d1bf8b724a486b9ad83625bec91607
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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