Phosphorus oxychloride → HCID 59427361, compound

HRID 1013657Notes

Reaction equation

HRID 1013657 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=O)[NH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=2)=[N:9][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67017182HCID 67017182, compound

Product 1

HCID 59427361HCID 59427361, compound

Conditions

Temperature
0 °C

Procedure

A dry RBF set up with stirring bar and reflux condenser was charged with 4-(6-methylpyridin-2-yl)phthalazin-1(2H)-one (780 mg, 3.29 mmol) and POCl3(10.7 ml, 115 mmol). This was stirred under reflux for 18 h. Excess POCl3 was removed under vacuum with an aid of toluene. The residue was cooled to 0° C. and basified with cold 6 N NaOH until pH=9. Occasionally, ice was added to keep the mixture cold to prevent the hydrolysis. Stirring, agitation, and sonication eventually provided a solid material at basic pH. The solids were filtered, washed with ample amount of water and dried under vacuum to afford a white solid. MS Calcd for C14H10ClN3: [M]+=255. Found: [M+H]+=256.

Workup

  1. temperaturereflux condenser
  2. stirringThis was stirred
  3. temperatureunder reflux for 18 h
  4. customExcess POCl3 was removed under vacuum with an aid of toluene
  5. additionOccasionally, ice was added
  6. customthe hydrolysis
  7. stirringStirring
  8. customagitation, and sonication
  9. customeventually provided a solid material at basic pH
  10. filtrationThe solids were filtered
  11. washwashed with ample amount of water
  12. customdried under vacuum
  13. customto afford a white solid

Sources & evidence

ORD record
ord-758164381d6e4e3e9e8dce375194dd92
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

Loading…