Triethylamine → HCID 178498348, compound

HRID 1649704Notes

Reaction equation

HRID 1649704 reaction equation
C(N(CC)CC)C.[F:8][CH:9]([F:32])[C:10]1[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[C:13]([C:20]([O:22][CH2:23]C)=[O:21])=[C:12]([O:25]CC)[C:11]=1[C:28]([O:30][CH3:31])=[O:29].[OH-].[K+].S(Cl)(Cl)=O>CCO.CCOCC.[Pd].CO.O>[F:32][CH:9]([F:8])[C:10]1[C:11]([C:28]([O:30][CH3:31])=[O:29])=[C:12]([OH:25])[C:13]([C:20]([O:22][CH3:23])=[O:21])=[C:14]([C:16]([F:19])([F:17])[F:18])[N:15]=1

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 14013780HCID 14013780, compound

Product 1

HCID 178498348HCID 178498348, compoundYield 32%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Product of Example 18 (23.34 g, 0.032 mol), 9.0 ml (0.064 mol) of triethylamine and 0.62 g of Pd/C (10%) in 100 ml of EtOH were reacted as described by the preparation of product of Example 22 affording 9.99 g of dark orange oil. A portion of this oil (5.0 g, 0.014 mol), 4.51 g (0.070 mol) of 87% KOH, 1 ml of H2O in 30 ml of EtOH was stirred at reflux for 5 days. Reaction mixture was concentrated and the residue was poured into water and washed with ether. The aqueous layer was acidified with conc HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo to 4.26 g of foamy oil. This oil was treated as described in Example 19: 4.26 g (0.013 mol) of this foamy oil, 25 ml of thionyl chloride and 25 ml of MeOH were reacted affording a dark solid residue which was taken up in ether and extracted with 15% K2CO3 and water, acidified with concentrated HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo in 2.7 g of solid. Recrystallization from hexane-ether afforded 1.37 g (32.0%) of product as a tan solid: mp 83°-84.5° C.

Workup

  1. temperatureat reflux for 5 days
  2. customReaction mixture
  3. concentrationwas concentrated
  4. additionthe residue was poured into water
  5. washwashed with ether
  6. extractionextracted with ether
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo to 4.26 g of foamy oil
  9. additionThis oil was treated
  10. customaffording a dark solid residue which
  11. extractionextracted with 15% K2CO3 and water
  12. extractionextracted with ether
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated in vacuo in 2.7 g of solid
  15. customRecrystallization from hexane-ether

Sources & evidence

ORD record
ord-48485c0b882e414f9820ef6ff14ef067
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

Loading…