Hydrochloric Acid → HCID 13882880, compound

HRID 542117Notes

Reaction equation

HRID 542117 reaction equation
[Cl:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16]C)=[O:14])=[C:5](O)[CH:4]=1.[OH-].[K+].Cl.N1C(C)=CC=CC=1C.O=P(Cl)(Cl)[Cl:34]>C(O)C.O>[Cl:34][C:5]1[CH:4]=[C:3]([C:2]([Cl:1])([F:20])[F:19])[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 14797Potassium HydroxideHCID 24813Phosphorus oxychlorideHCID 178470033HCID 178470033, compound

Product 1

HCID 13882880HCID 13882880, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 5.0 g (0.016 mol) of product of Example 5, 8.38 g (0.154 mol) of KOH, 45 ml of water in 100 ml of ethanol were refluxed for 16 hours. The reaction mixture was poured into 250 ml of water containing 50 ml of HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo to 3.35 g of solid. Then 45 ml of SOCl2 was added to the solid and this was refluxed for 2 hours. Reaction mixture was concentrated in vacuo and 45 ml of methanol was added to the residue and refluxed for 16 hours. Reaction mixture was concentrated in vacuo. The residue was dissolved in ether, extracted with 10% K2CO3, and water. The combined aqueous layers were acidified with concentrated HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo to 2.11 g of white solid. To this solid was added 1.21 ml (0.010 mol) of 2,6 -lutidine and 20 ml of POCl3. This was refluxed for 16 hours. The reaction mixture was concentrated in vacuo. The residue was poured into water, extracted with ether, washed with 10% HCl, dried (MgSO4) and concentrated in vacuo to 2.17 g of brown oil. Then 50 ml of MeOH was added and this was refluxed for 31/2 hours and then stirred at room temperature for 72 hours. The reaction mixture was concentrated in vacuo to 1.88 g of crude produt. Kugelrohr distillaton at 47 Pa, pot temperature 80° C., afforded 1.55 g (68.3%) of product as a clear oil, nD25 1.4493.

Workup

  1. temperaturewere refluxed for 16 hours
  2. extractionextracted with ether
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to 3.35 g of solid
  5. additionThen 45 ml of SOCl2 was added to the solid
  6. temperaturethis was refluxed for 2 hours
  7. customReaction mixture
  8. concentrationwas concentrated in vacuo and 45 ml of methanol
  9. additionwas added to the residue
  10. temperaturerefluxed for 16 hours
  11. customReaction mixture
  12. concentrationwas concentrated in vacuo
  13. dissolutionThe residue was dissolved in ether
  14. extractionextracted with 10% K2CO3, and water
  15. extractionextracted with ether
  16. dry with materialdried (MgSO4)
  17. concentrationconcentrated in vacuo to 2.11 g of white solid
  18. temperatureThis was refluxed for 16 hours
  19. concentrationThe reaction mixture was concentrated in vacuo
  20. additionThe residue was poured into water
  21. extractionextracted with ether
  22. washwashed with 10% HCl
  23. dry with materialdried (MgSO4)
  24. concentrationconcentrated in vacuo to 2.17 g of brown oil
  25. additionThen 50 ml of MeOH was added
  26. temperaturethis was refluxed for 31/2 hours
  27. concentrationThe reaction mixture was concentrated in vacuo to 1.88 g of crude produt

Sources & evidence

ORD record
ord-a0f72e0ee22940d49b4119ac4d58e3c6
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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