P-Anisidine → HCID 10476669, compound

HRID 1293469Notes

Reaction equation

HRID 1293469 reaction equation
[CH:1]([N:3]1[C:15]2[C:14]([O:16][CH3:17])=[CH:13][CH:12]=[C:11]([S:18](Cl)(=[O:20])=[O:19])[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:2].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:1]([N:3]1[C:15]2[C:14]([O:16][CH3:17])=[CH:13][CH:12]=[C:11]([S:18]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:2]

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 85966947HCID 85966947, compound

Product 1

HCID 10476669HCID 10476669, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Intermediate 63 (0.2 g, 0.62 mM) was dissolved in 40 ml of chloroform. To it was added p-anisidine (0.21 g, 1.66 mM), 0.19 g triethylamine and the reaction was refluxed for 18 hrs. Solvent was evaporated and the residue was extracted in ethyl acetate. The organic layer was washed with 10% HCl solution, brine and then dried over anhydrous Na2SO4. It was then evaporated to obtain the crude residue which was then purified over silica gel column using ethylacetate-hexane system to obtain the desired compound as beige solid with a yield of 65% (0.16 g); mp 190-192° C.

Workup

  1. temperaturethe reaction was refluxed for 18 hrs
  2. customSolvent was evaporated
  3. extractionthe residue was extracted in ethyl acetate
  4. washThe organic layer was washed with 10% HCl solution, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customIt was then evaporated
  7. customto obtain the crude residue which
  8. customwas then purified over silica gel column

Sources & evidence

ORD record
ord-9be862be32d44b87b62f562413e2d3c1
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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