Pyridine → HCID 23123796, compound

HRID 1527620Notes

Reaction equation

HRID 1527620 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].N1C=CC=CC=1.Cl[C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21].C(OCC)(=O)C>O1CCCC1.O>[Cl:25][C:24]([Cl:27])([Cl:26])[CH2:23][O:22][C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:21]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 11400Ethyl 3-aminobenzoateHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 23123796HCID 23123796, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution prepared by adding 1.0 g of ethyl m-aminobenzoate and 0.72 g of pyridine to 10 ml of tetrahydrofuran and stirring the resultant mixture at room temperature was dropwise added a solution of 1.55 g of 2,2,2-trichloroethyl chloroformate in 5 ml of tetrahydrofuran. After the resultant mixture was stirred for 2 hours, ethyl acetate and water were added to the reaction solution, and a separating operation was performed. Then, an organic layer was separated and dried with anhydrous magnesium sulfate. The solution was filtered, and then the filtrate was collected, and the solvent of the filtrate was distilled off under reduced pressure. The residue was washed with hexane to obtain 1.89 g (yield 91%) of the title compound.

Workup

  1. customTo a solution prepared
  2. customThen, an organic layer was separated
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationThe solution was filtered
  5. customthe filtrate was collected
  6. distillationthe solvent of the filtrate was distilled off under reduced pressure
  7. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-c13a717ad6ec484da129db3d747167d1
Source dataset
uspto-grants-2015_07
Patent number
US09089133B2

Reaction notes

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