Chlorine monoxide → HCID 22612415, compound

HRID 844042Notes

Reaction equation

HRID 844042 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[O:5][C:6]1[N:23]=[CH:22][CH:21]=[CH:20][C:7]=1[C:8]([NH:10][CH2:11][CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.O(Cl)Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[O:5][C:6]1[C:7]([C:8]2[O:19][CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]=2)=[CH:20][CH:21]=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 24646Chlorine monoxideHCID 22612127HCID 22612127, compound

Product 1

HCID 22612415HCID 22612415, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(3-Chloro-phenoxy)-N-(2-hydroxy-2-phenyl-ethyl)-nicotinamide (0.320 grams, 0.868 mmole) and phosprorus oxychloride (0.7 ml) in toluene (10 ml) was stirred over night. The mixture was concentrated to dryness and dissolved in methanol (10 ml) and potassium carbonate was added. The mixture was stirred for 2 hours at room temperature and refluxed for 30 minutes. The methanol was evaporated, and the residue taken up in ethyl acetate. It was washed with water and brine, dried over Na2SO4, and concentrated to give a product that was purified by chromatography on silica gel eluting with 1/3 ethyl acetate/hexane to give a pale yellow oil (0.102 g). HRMS 351.0897; 1H NMR (400 MHz, CDCl3) d 4.06 (dd, J=8.1, 15.0 Hz, 1H), 4.56 (dd, J=10.3, 15.0 Hz, 1H), 5.66 (dd, J=8.0, 10.3 Hz, 1H), 7.24 (m, 10H), 8.8.27 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutiondissolved in methanol (10 ml)
  3. additionpotassium carbonate was added
  4. temperaturerefluxed for 30 minutes
  5. customThe methanol was evaporated
  6. washIt was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customto give a product that
  10. customwas purified by chromatography on silica gel eluting with 1/3 ethyl acetate/hexane

Sources & evidence

ORD record
ord-34a1c99fcd8940f6871f1e303989fdee
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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