Triethylamine → HCID 10046153, compound

HRID 1293471Notes

Reaction equation

HRID 1293471 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].C([N:24]([CH2:27][CH3:28])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:24][C:27]3[CH:28]=[CH:4][C:9]([CH3:10])=[CH:8][CH:7]=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

4

Reactant 2

HCID 8471TriethylamineHCID 85966947HCID 85966947, compound

Product 1

HCID 10046153HCID 10046153, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Intermediate 63 (0.2 g, 0.62 mM) was dissolved in 50 ml of chloroform. To it was added p-toludine (0.165 g, 1.54 mM) and 0.16 g triethylamine. The reaction was refluxed for 15 hrs. Solvent was evaporated and the residue was taken up in ethyl acetate. The organic layer was washed with 10% HCl solution, brine and then dried over anh 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 75% (0.18 g); mp 193-199° C.

Workup

  1. temperatureThe reaction was refluxed for 15 hrs
  2. customSolvent was evaporated
  3. washThe organic layer was washed with 10% HCl solution, brine
  4. dry with materialdried over anh Na2SO4
  5. customIt was then evaporated
  6. customto obtain the crude residue which
  7. customwas then purified over silica gel column

Sources & evidence

ORD record
ord-7fc2a415bb5f4bb7a1e0d1a50caa2c56
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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