Chlorine monoxide → HCID 54499931, compound

HRID 844041Notes

Reaction equation

HRID 844041 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][C@@H:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:12][OH:13])=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:13][CH2:12][C@H:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:10]=2)=[CH:20][CH:21]=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 24646Chlorine monoxideHCID 53928193HCID 53928193, compound

Product 1

HCID 54499931HCID 54499931, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (S)-2-(3-Chloro-phenoxy)-N-(2-hydroxy-1-phenyl-ethyl)-nicotinamide (0.340 grams, 0.922 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 (0.013 g); HRMS 351.0917; M.P. 78-80° C.; Anal. calcd. for C20H15N2O2Cl: C, 57.37;H, 3.74; N, 7.42. Found: C, 57.31; H, 3.80; N, 7.39.

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-4bf639e5e83c4b9dad11673837f8eaed
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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