Phosphorus oxychloride → HCID 87741012, compound

HRID 1027874Notes

Reaction equation

HRID 1027874 reaction equation
[NH2:1][C:2]1[N:16]=[C:15](O)[C:5]2[CH2:6][CH2:7][O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]=2[N:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:15]1[C:5]2[CH2:6][CH2:7][O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]=2[N:3]=[C:2]([NH2:1])[N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178508873HCID 178508873, compound

Product 1

HCID 87741012HCID 87741012, compound

Procedure

A mixture of Example 29C (0.63 g, 2.7 mmol) and phosphorus oxychloride (10 mL) was heated at reflux for 1 hour, cooled, concentrated under reduced pressure followed by the addition of water (20 mL). The mixture was filtered and the resulting solid was taken up in 1 M HCl (20 mL) and heated at reflux for 5 minutes. The cooled mixture was basified with 1M NaOH and extracted with CH2Cl2 (3×), filtering each extraction through diatomaceous earth. The combined CH2Cl2 layers were dried (MgSO4), filtered, concentrated under reduced pressure and chromatographed on silica gel eluting with a gradient of CH2Cl2:EtOAc (20:1 and 10:1) to provide the title compound. 1H NMR (CDCl3) δ 2.94 (t, J=6.10 Hz, 2H), 4.52 (t, J=6.27 Hz, 2H), 5.15 (s, 2H), 7.13 (dd, J=7.97, 1.19 Hz, 1H), 7.21-7.30 (m, 1H), 7.41-7.49 (m, 1H), 7.82 (dd, J=7.80, 1.70 Hz, 1H); MS (M+H)+ m/z 248.

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionfollowed by the addition of water (20 mL)
  5. filtrationThe mixture was filtered
  6. temperatureheated
  7. temperatureat reflux for 5 minutes
  8. extractionextracted with CH2Cl2 (3×)
  9. filtrationfiltering
  10. extractioneach extraction through diatomaceous earth
  11. dry with materialThe combined CH2Cl2 layers were dried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customchromatographed on silica gel eluting with a gradient of CH2Cl2:EtOAc (20:1 and 10:1)

Sources & evidence

ORD record
ord-a389078400d34a06bd99555c818531d1
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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