Hydrochloric Acid → HCID 22445845, compound

HRID 2375350Notes

Reaction equation

HRID 2375350 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10](=[O:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>[N+](C1C=CC=CC=1)([O-])=O>[C:13]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][NH:9][C:10](=[O:12])[CH3:11])=[CH:2][CH:3]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 70143N-(2-phenylethyl)acetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22445845HCID 22445845, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

N-(2-Phenylethyl)acetamide (49.01 mmol, 8.00 g) was introduced into nitrobenzene (40 ml). Benzoyl chloride (54.07 mmol, 7.60 g) was added thereto and then, at room temperature, aluminum tri-chloride (73.52 mmol, 9.80 g) was introduced in portions. The mixture was then heated at 50° C. for 8 h. The reaction mixture was poured into a mixture of ice and concentrated hydrochloric acid, and nitrobenzene was removed by steam distillation. The aqueous residue was extracted with ethyl acetate. The residue after concentration of the organic phase was chromatographed on silica gel (mobile phase dichloromethane/methanol (3% by volume)), resulting in 4.5 g of the title compound as orange oil.

Workup

  1. customwas removed by steam distillation
  2. extractionThe aqueous residue was extracted with ethyl acetate
  3. customThe residue after concentration of the organic phase was chromatographed on silica gel (mobile phase dichloromethane/methanol (3% by volume))

Sources & evidence

ORD record
ord-cbb5fc12478c4562bac866e9c577c191
Source dataset
uspto-grants-2008_12
Patent number
US07465744B2

Reaction notes

Loading…