Triethylamine → HCID 86616533, compound

HRID 1932484Notes

Reaction equation

HRID 1932484 reaction equation
C1[O:19][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][N:13]=3)=[CH:7][CH:6]=2)OC1.C(N(CC)CC)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:31](Cl)=[O:32]>C1COCC1>[CH:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:31](=[O:32])[C:30]3[CH:34]=[CH:35][C:36]([Cl:37])=[C:28]([Cl:27])[CH:29]=3)=[CH:14][N:13]=2)=[CH:9][CH:10]=1)=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 68525710HCID 68525710, compound

Product 1

HCID 86616533HCID 86616533, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 4-[(5-amino-2-pyridyl)oxy]benzaldehyde ethylene acetal (5.27 g, 20.4 mmol) and triethylamine (3.41 mL, 24.5 mmol) in THF (80 mL) was added dropwise a solution of 3,4-dichlorobenzoyl chloride (4.49 g, 21.4 mmol) in THF (30 mL) under ice cooling. The resulting solution was stirred for 2 hours at the same temperature. The reaction solution was concentrated under reduced pressure, to the residue, 80% acetic acid (55 mL) was added, and the mixture was heated at 80° C. with stirring for 1 hour. The reaction solution was concentrated under reduced pressure and to the residue was added water, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated. The obtained solid was recrystallized from isopropanol, to thereby yield 5.63 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, to the residue, 80% acetic acid (55 mL)
  2. additionwas added
  3. stirringwith stirring for 1 hour
  4. concentrationThe reaction solution was concentrated under reduced pressure and to the residue
  5. additionwas added water
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customThe obtained solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-d5bae46bf40c4dcda02f8e9eb120a420
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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