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Volumn 51, Issue 9, 2010, Pages 1265-1268

Synthesis of 1,2 diamines under environmentally benign conditions: application for the preparation of imidazolidiniums

Author keywords

1,2 Diamines; Imidazolidinium

Indexed keywords

1,2 DIAMINE DERIVATIVE; ALCOHOL; CARBENOID; DIAMINE DERIVATIVE; IMIDAZOLIDINE DERIVATIVE; IMIDAZOLIDINIUM DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 74749104599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.072     Document Type: Article
Times cited : (16)

References (67)
  • 30
    • 38849161554 scopus 로고    scopus 로고
    • For review see:
    • For review see:. Kizirian J.-C. Chem. Rev. 108 (2008) 140
    • (2008) Chem. Rev. , vol.108 , pp. 140
    • Kizirian, J.-C.1
  • 62
    • 74749091661 scopus 로고    scopus 로고
    • note
    • Typical experimental procedure for N-monoalkylation of amines in water: 2,4,6-trimethylaniline (8.45 mL, 60 mmol) and 1,2-dibromoethane (6.15 g, 30 mmol) were sequentially added at room temperature to water (15 mL). The two-layered solution was vigorously stirred at 95 °C overnight. The solution was cooled to room temperature and 15 mL of water was added. Extraction with 3 × 15 mL of EtOAc and evaporation of the aqueous phase furnished a brown solid which was recrystallized from MeOH/EtOAc to yield 7.1 g (21 mmol, 70%) of 15a as a white solide.
  • 63
    • 74749102007 scopus 로고    scopus 로고
    • note
    • Ethanol and isopropanol were also tested but with poor success.
  • 64
    • 74749108526 scopus 로고    scopus 로고
    • note
    • Procedure for the preparation of (N,N′-dicyclohexyl) 1,2-ethanediamine dihydrobromide 21d in alcoholic solvent: Cyclohexylamine (20.0 g, 202 mmol, 3.0 equiv) and 1,2-dibromoethane (12.6 g, 67.0 mmol, 1.0 equiv) were sequentially added at room temperature to methanol (50 mL). The solution was vigorously stirred under reflux overnight. The solution was evaporated under reduced pressure to furnish a brown solid which was triturated with acetone (40 ml), filtrated, and washed with acetone to yield 16.7 g of compound 21d as a white solid (65%).
  • 66
    • 0033598258 scopus 로고    scopus 로고
    • For SIMes,HCl, see Ref. 5For SIAd, HCl, see:
    • For SIMes,HCl, see Ref. 5For SIAd, HCl, see:. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
    • (1999) Org. Lett. , vol.1 , pp. 953
    • Scholl, M.1    Ding, S.2    Lee, C.W.3    Grubbs, R.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.