p-Toluenesulfonic acid → HCID 178429643, compound

HRID 1821354Notes

Reaction equation

HRID 1821354 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.[CH3:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[CH:25]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2/[N:18]=[CH:25]/[C:21]2[S:22][CH:23]=[CH:24][C:20]=2[CH3:19])=[N:2]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 799113-Methyl-2-thiophenecarboxaldehydeHCID 69001756HCID 69001756, compound

Product 1

HCID 178429643HCID 178429643, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Compound 2 (0.060 g, 0.25 mmol) was dissolved in toluene (3.0 mL) and the solution was added with 3-methylthiophene-2-carbaldehyde (55 μL, 0.51 mmol), p-toluenesulfonic acid (small amount), followed by stirring at 60° C. for 2 hours. Then, the reaction mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in ethanol to obtain Compound 160 (76 mg, 88%).

Workup

  1. extractionThen, the reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated in ethanol

Sources & evidence

ORD record
ord-f2416d6818f041aa81a3fe31a73f2f29
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…