p-Toluenesulfonic acid → HCID 66743595, compound

HRID 2363976Notes

Reaction equation

HRID 2363976 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[S:16]1(=[O:24])(=[O:23])[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:19]4([CH2:20][CH2:21][S:16](=[O:24])(=[O:23])[CH2:17][CH2:18]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 2622301,1-Dioxo-tetrahydro-thiopyran-4-oneHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 66743595HCID 66743595, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.050 g, 0.23 mmol) in acetic acid (3 mL) were added tetrahydro-4H-thiopyran-4-one 1,1-dioxide (0.068 g, 0.46 mmol) and p-toluenesulfonic acid (0.0040 g, 0.023 mmol). The mixture was heated at 80° C. overnight. Then, the solvent was removed and the obtained residue was taken up in methanol (20 mL). Solid NaHCO3 (1.5 g) was added, and the mixture was stirred for 10 min. The cloudy suspension was filtered and the collected solids were washed with methanol (20 mL) followed by water (30 mL) to give the title compound (0.0195 g, 24%) as a yellow solid:

Workup

  1. customThen, the solvent was removed
  2. additionSolid NaHCO3 (1.5 g) was added
  3. filtrationThe cloudy suspension was filtered
  4. washthe collected solids were washed with methanol (20 mL)

Sources & evidence

ORD record
ord-591ea1204f9b42659e89d595606b6681
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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