Acetone → HCID 66743809, compound

HRID 2363931Notes

Reaction equation

HRID 2363931 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([NH2:16])=[O:15].O.[C:18]1(C)[CH:23]=CC(S(O)(=O)=O)=C[CH:19]=1.CC(C)=O>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:3]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=3)[S:5][C:4]=2[C:14](=[O:15])[NH:16][C:18]1([CH3:23])[CH3:19]

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 66743384HCID 66743384, compound

Product 1

HCID 66743809HCID 66743809, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(methylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (400 mg, 1.72 mmol), p-toluenesulfonic acid monohydrate (150 mg) and acetone (40 mL) in toluene (40 mL) was heated to reflux overnight. After removal of the solvent, the residue was purified by column chromatography on silica gel (MeOH: dichloromethane=1:9) to afford the title compound (30 mg, yield 6%) as an orange solid:

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography on silica gel (MeOH: dichloromethane=1:9)

Sources & evidence

ORD record
ord-01ae5a83cc184c86809eaa12a90628a0
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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