Pyridine → HCID 23123796, compound

HRID 1694629Notes

Reaction equation

HRID 1694629 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-54e2abf22273483d91730f316faf05c2
Source dataset
uspto-grants-2012_04
Patent number
US08158814B2

Reaction notes

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