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Volumn 35, Issue 1, 1998, Pages 249-255

Synthesis of the Methanesulfonates of α-(4-Chlorophenyl)-α-[1-(2-chlorophenyl)ethenyl]-1H-1,2,4-triazole- 1-ethanol and α-[1-(2-Chlorophenyl)ethenyl]-α-(2,4-difluorophenyl)- 1H-1,2,4-triazole-1-ethanol, Aloha Styryl Carbinol Antifungal Agents

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 3 (2 CHLOROPHENYL) 2 (4 CHLOROPHENYL) 1 (1H 1,2,4 TRIAZOL 1 YL) 3 BUTEN 2 OL; ALPHA[1 (2 CHLOROPHENYL)ETHENYL] ALPHA (2,4 DIFLUOROPHENYL) 1H 1,2,4 TRIAZOLE 1 ETHANOL; ANTIFUNGAL AGENT; BASE; CINNAMYL ALCOHOL; DUP 991; MESYLIC ACID DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0031916586     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350144     Document Type: Article
Times cited : (4)

References (47)
  • 7
    • 1542536387 scopus 로고    scopus 로고
    • US Patent 4,952,232 (1990)
    • [c] J. Cuomo, R. S. Greenberg and R. E. Olson, US Patent 4,952,232 (1990); Chem. Abstr., 112, 50601 (1990);
    • Cuomo, J.1    Greenberg, R.S.2    Olson, R.E.3
  • 8
    • 1542536385 scopus 로고
    • [c] J. Cuomo, R. S. Greenberg and R. E. Olson, US Patent 4,952,232 (1990); Chem. Abstr., 112, 50601 (1990);
    • (1990) Chem. Abstr. , vol.112 , pp. 50601
  • 10
    • 1542641256 scopus 로고
    • Recent Developments in the Chemistry of Azole Fungicides
    • BCPC Publications, Croydon
    • For example, flutriafol has been prepared via both routes: P. A. Worthington in Recent Developments in the Chemistry of Azole Fungicides, Proceedings of 1984 British Crop Protection Conference, Pests and Diseases, Vol 3, BCPC Publications, Croydon, 1984, pp 955-962.
    • (1984) Proceedings of 1984 British Crop Protection Conference, Pests and Diseases , vol.3 , pp. 955-962
    • Worthington, P.A.1
  • 11
    • 1542746544 scopus 로고    scopus 로고
    • note
    • The article describes the preparation of 1a. The fluoro analog 1b was prepared by substituting difluoroacetophenone in place of 2,4′-dichloroacetophenone. The procedure was essentially identical to that of 1a
  • 16
    • 0002226325 scopus 로고
    • R. Adams, ed, John Wiley & Sons Inc, New York
    • [7a] T.L. Jacobs in Organic Reactions, Vol 5, R. Adams, ed, John Wiley & Sons Inc, New York, 1949, pp 20-22;
    • (1949) Organic Reactions , vol.5 , pp. 20-22
    • Jacobs, T.L.1
  • 25
    • 1542641270 scopus 로고    scopus 로고
    • note
    • About 5% of the total reactants volume was present in the reaction vessel at any one time.
  • 26
    • 1542746539 scopus 로고    scopus 로고
    • note
    • The heat of reaction was determined to be -42 kcal/mole for dichloroacetophenone to produce a typical mixture of chlorohydrin 2a and oxirane 8a via the co-feed route. Reactions that formed largely 8a seemed to be more exothermic.
  • 27
    • 1542431585 scopus 로고    scopus 로고
    • note
    • On a kilolab scale (221) using a batch process, the yields from 4a were 40-45%.
  • 28
    • 1542536383 scopus 로고    scopus 로고
    • note
    • Sozzani and coworkers [23] have demonstrated the value of polyethylene glycols as good solvents for both organic substrates and inorganic salts, in particular potassium salts. Although a wide variety of chemistry is possible in these solvents[24], a literature search indicated the field has been but little exploited. Polyethylene glycol of average molecular weight 300 possessed an attractive combination of solubility, viscosity, toxicity, and cost within our process, and was chosen as the co-solvent. [14] Other potassium bases, such as bicarbonate, hydroxide, bis(trimethylsilyl)amide, and methoxide produced inferior results. Since charging the potassium salt of triazole in place of t-butoxide produced very similar results, it could be assumed that the triazole anion would be both sufficiently basic and nucleophilic to drive the two reactions to 9a.
  • 35
    • 1542536381 scopus 로고    scopus 로고
    • note
    • Efficient methods to prepare l-phenacyl-1H,1,2,4-triazoles from 4-amino-l,2,4-triazole have recently been published: see references 9 and 19, and references cited therein.
  • 37
    • 1542431577 scopus 로고    scopus 로고
    • note
    • [b] The control of regioselectivity, specifically of potentially valuable β-hydroxyethyl(l,2,4-triazole) derivatives, has been examined extensively and several innovative methods are now available to the process chemist [25].
  • 39
    • 1542431573 scopus 로고    scopus 로고
    • note
    • The direct addition of methanesulfonic acid to the reaction mixture formed la but it couldn't be efficiently isolated from the black, viscous mixture.
  • 40
    • 1542431578 scopus 로고    scopus 로고
    • note
    • Analysis by gc: DB1-30 column, 30 m x 0.32 mm, carrier He, program: 2 minutes at 50°, 10°/minute up to 240°.
  • 41
    • 1542431574 scopus 로고    scopus 로고
    • note
    • [22a] Novapack C18 column, 45% 0.05 M sodium dihydrogen phosphate/55% acetonitrile, 225 nm;
  • 42
    • 1542746533 scopus 로고    scopus 로고
    • note
    • [b] ES Industries column, A: 0.1% triethylamine/0.1% phosphoric acid in water adjusted to pH 3.0 with sodium hydroxide, B: acetonitrile; gradient elution%B increasing from 55 to 90%; 225 nm.
  • 46
    • 1542536380 scopus 로고    scopus 로고
    • US Patent 4404216 (1983)
    • K. Richardson, US Patent 4404216 (1983); Chem. Abstr., 99, 38467 (1983).
    • Richardson, K.1
  • 47
    • 4243847727 scopus 로고
    • K. Richardson, US Patent 4404216 (1983); Chem. Abstr., 99, 38467 (1983).
    • (1983) Chem. Abstr. , vol.99 , pp. 38467


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.