Hydrochloric Acid → HCID 58175692, compound

HRID 2041826Notes

Reaction equation

HRID 2041826 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH2:19][CH3:20])[CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)=O.CO[CH:34](OC)[CH2:35][NH2:36].Cl>CC(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([N:10]2[CH:34]=[CH:35][N:36]=[C:11]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH2:19][CH3:20])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 58175621HCID 58175621, compound

Product 1

HCID 58175692HCID 58175692, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 250 mL round-bottom flask added N-(4-bromo-2,6-diethylphenyl)benzamide (7.64 g, 23 mmol), phosphorus pentachloride (4.79 g, 23 mmol), and phosphorus oxychloride (40 mL). The reaction was heated up to reflux under nitrogen. After 2.5 h, the reaction mixture was cooled and phosphorus oxychloride was distilled off using short path distillation apparatus. 2-propanol (40 mL) and 2,2-dimethoxyethanamine (48.4 g, 460 mmol) was added. The reaction was stirred at room temperature for 4 h. Concentrated hydrochloric acid (40 mL) was added carefully, and the reaction was heated to reflux overnight. The solution was decanted from black solid and neutralized with 10% sodium hydroxide solution, extracted with ethyl acetate. The organic layers were dried over magnesium sulfate. The residue was purified by silica gel column chromatography eluting with 20 and 30% ethyl acetate/hexanes. 6.75 g (83% yield) of product was obtained after purification.

Workup

  1. temperatureThe reaction was heated up
  2. temperatureto reflux under nitrogen
  3. temperaturethe reaction mixture was cooled
  4. distillationphosphorus oxychloride was distilled off
  5. distillationpath distillation apparatus
  6. temperaturethe reaction was heated
  7. temperatureto reflux overnight
  8. customThe solution was decanted from black solid and neutralized with 10% sodium hydroxide solution
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layers were dried over magnesium sulfate
  11. customThe residue was purified by silica gel column chromatography
  12. washeluting with 20 and 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-bfe6a05f8cc24541a7d3ce8e540c0e01
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

Loading…