Acetone → HCID 66744094, compound

HRID 2363966Notes

Reaction equation

HRID 2363966 reaction equation
[CH2:1]([NH:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[S:11][C:10]=1[C:20]([NH2:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24]([CH3:26])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([N:8]1[C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[S:11][C:10]=2[C:20](=[O:21])[NH:22][C:24]1([CH3:26])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 66744081HCID 66744081, compound

Product 1

HCID 66744094HCID 66744094, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(benzylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.124 g, 0.400 mmol), acetone (3.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 3 days at 70° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate (100 mL, 50 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to ethyl acetate), then triturated with ethyl acetate/hexanes (1:1), and the precipitate was collected by filtration to afford the title compound (0.0841 g, 60%) as a yellow solid:

Workup

  1. extractionExtraction with ethyl acetate (100 mL, 50 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThis oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to ethyl acetate)
  5. customtriturated with ethyl acetate/hexanes (1:1)
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-10a49117f2c245639e7a16c4492bbd19
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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