Aluminum(III) Chloride → N-(1-Oxo-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide

HRID 904816Notes

Reaction equation

HRID 904816 reaction equation
[C:1]([NH:9][C@H:10]([C:19]([OH:21])=O)[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(OC(=O)C)(=O)C.C(=S)=S>[C:1]([NH:9][CH:10]1[CH2:11][CH2:12][C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]1=[O:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 22824842HCID 22824842, compound

Product 1

HCID 13293063N-(1-Oxo-1,2,3,4-tetrahydronaphthalen-2-yl)benzamideYield 817.4%

Reagents, catalysts & solvents 2

HCID 6348Carbon DisulfideSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of N-benzoyl homophenylalanine (4.4 g, 1.66 mmole) in acetic anhydride (60 ml) was heated on the steam bath for 1/2 hr. The solvent was removed in vacuo, the resulting oil was dissolved in CS2 and then added to a suspension of AlCl3 (6.2 g, 4.6 mmoles) in CS2 (60 ml). This mixture was heated at reflux for 1 hr, the solvent was removed in vacuo and ice was added to the residue. The reaction mixture was extracted with ethyl acetate, the ethyl acetate layer was washed with brine, dried over Na2SO4 and evaporated to dryness to afford 3.6 g (88%) of product, m.p. 175° C. After recrystallization from toluene it had m.p. 175°-178° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resulting oil was dissolved in CS2
  3. temperatureThis mixture was heated
  4. temperatureat reflux for 1 hr
  5. customthe solvent was removed in vacuo and ice
  6. additionwas added to the residue
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe ethyl acetate layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-a4a5d12ba0594f4fbf16ba85a740e3aa
Source dataset
uspto-grants-1983_12
Patent number
US04420480

Reaction notes

Loading…