Phosphorus oxychloride → HCID 22612301, compound

HRID 844047Notes

Reaction equation

HRID 844047 reaction equation
O[CH:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[O:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:20]1([CH:2]2[O:19][C:5]([C:6]3[C:7]([O:12][C:13]4[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=4)=[N:8][CH:9]=[CH:10][CH:11]=3)=[N:4][CH2:3]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22612212HCID 22612212, compound

Product 1

HCID 22612301HCID 22612301, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N-(2-Hydroxy-2-phenyl-ethyl)-2-(pyridin-3-yloxy)-nicotinamide (0.450 grams, 1.3 mmole) and phosphorus oxychloride (1.25 ml, 13 mmole) in toluene (5 ml) was stirred over night. The mixture was concentrated to dryness and dissolved in methanol (5 ml) and potassium carbonate (0.500 g) was added. The mixture was stirred at room temperature over night. The mixture was poured into water and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over Na2SO4, and concentrated to give an oil that was purified by chromatography on silica gel eluting with ethyl acetate to give a colorless oil (0.042 g). HRMS 318.1269; 1H NMR (400 mHz, CDCl3) d 4.09 (dd, J=15.1 Hz, 8.1 Hz, 6H), 4.57 (dd, J=15.1 Hz, 10.3 Hz, 1H), 5.67 (dd, J=10.2 Hz, 7.9 Hz, 1H), 7.09-7.13 (m, 1H), 7.32-7.39 (m, 6H), 7.54-7.57 (m, 1H), 8.20-8.22 (m, 1H), 8.29-8.31 (m, 1H), 8.46 (dd, J=4.6 Hz, 1.0 Hz, 1H), 8.61-8.64 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutiondissolved in methanol (5 ml)
  3. additionpotassium carbonate (0.500 g) was added
  4. additionThe mixture was poured into water
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto give an oil that
  10. customwas purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-061924e1d521475b9f44d852e8d6f6a1
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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