Hydrochloric Acid → HCID 58175669, compound

HRID 2041829Notes

Reaction equation

HRID 2041829 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:8]=[C:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:10]=1[NH:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)Cl.CO[CH:43](OC)[CH2:44][NH2:45].Cl.[OH-].[Na+]>C(O)(C)C>[CH2:1]([C:5]1[CH:6]=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:8]=[C:9]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:10]=1[N:11]1[CH:43]=[CH:44][N:45]=[C:12]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 58175601HCID 58175601, compound

Product 1

HCID 58175669HCID 58175669, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-(3,5-diisobutylbiphenyl-4-yl)benzamide (6.27 g, 16.3 mmol), phosphorus oxychloride (20 mL), and phosphorus pentachloride (3.40 g, 16.3 mmol) was stirred at reflux for 4 h. The phosphorus oxychloride was removed by vacuum distillation. To the crude imidoyl chloride was added isopropanol (40 mL) and aminoacetaldehyde dimethyl acetal (35 mL, 321 mmol). This was stirred at ambient temperature for 18 h after which time conc. HCl (75 mL) was added. This was stirred at reflux for 18 h. The mixture was neutralized with 1N NaOH to pH 9 and extracted with dichloromethane. The product was purified on a silica gel column. Elution first with dichloromethane then dichloromethane and ethyl acetate (9:1) gave the desired product which was recrystallized from hexane to give 3.64 g (55% yield) as a white solid. Structure was confirmed by LC-MS and 1H NMR.

Workup

  1. temperatureat reflux for 4 h
  2. customThe phosphorus oxychloride was removed by vacuum distillation
  3. additionwas added
  4. stirringThis was stirred
  5. temperatureat reflux for 18 h
  6. extractionextracted with dichloromethane
  7. customThe product was purified on a silica gel column
  8. washElution first with dichloromethane

Sources & evidence

ORD record
ord-3ea1b2a6215444af91fc010c87ca971b
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

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