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Volumn 10, Issue 16, 2008, Pages 3385-3388

Efficient synthesis of sulfonyl azides from sulfonamides

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; SULFONAMIDE; SULFONE;

EID: 54049093686     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8011088     Document Type: Article
Times cited : (40)

References (29)
  • 9
    • 61349131129 scopus 로고    scopus 로고
    • Compare 24 569 commericially available benzenesulfonamides versus 1385 commercially available benzenesulfonyl chlorides. SciFinder, version 2006, Chemical Abstracts Service: Columbus, OH, 2006. (as of January 8, 2008).
    • Compare 24 569 commericially available benzenesulfonamides versus 1385 commercially available benzenesulfonyl chlorides. SciFinder, version 2006, Chemical Abstracts Service: Columbus, OH, 2006. (as of January 8, 2008).
  • 11
    • 61349104138 scopus 로고    scopus 로고
    • Use of dichloromethane as a solvent with sodium azide is avoided to prevent inadvertent generation of the highly shock sensitive diazidomethane. See: Peet, N. P, Weintraub, P. M. Chem. Eng. News 1993, 71, 4
    • Use of dichloromethane as a solvent with sodium azide is avoided to prevent inadvertent generation of the highly shock sensitive diazidomethane. See: Peet, N. P.; Weintraub, P. M. Chem. Eng. News 1993, 71, 4.
  • 13
  • 15
    • 61349179290 scopus 로고    scopus 로고
    • 3, and the organic layer was removed. The aqueous layer was extracted with toluene (2 × 3.3 mL). The combined organic extracts were used immediately. A conservative estimate of 50% yield was used for subsequent experiments. See ref 11.
    • 3, and the organic layer was removed. The aqueous layer was extracted with toluene (2 × 3.3 mL). The combined organic extracts were used immediately. A conservative estimate of 50% yield was used for subsequent experiments. See ref 11.
  • 16
    • 61349173505 scopus 로고    scopus 로고
    • 3
    • CAUTION
    • 3.
    • 3
  • 18
    • 61349163410 scopus 로고    scopus 로고
    • To a mixture of sulfonamide 1 (1.43 g, 5.00 ramol, NaHCO3 (1.68. g, water (6 mL, and 1 M aq CuSO4 (0.20 mL) in a 25 mL Erlenmeyer flask was added a solution of freshly prepared TfN3 (10 mL, 0.75 M in toluene, 7.5 mmol, followed by 40 mL of t-BuOH. The flask was loosely capped, and the solution was stirred vigorously behind a blast shield for 18 h at room temperature. The reaction mixture was transferred to a larger round-bottom flask, rinsing with water and toluene. With xylenes in the collection flask, the volatiles were removed by a rotary evaporator, causing precipitation. Filtration afforded 2 as a yellow powder (1.45 g, 93% yield, mp 78.5-79.5 °C, Rf, 0.46 (silica gel, hexanes:EtOAc 8:2, vmax(KBr disc)/cm-1 2138 (N3, 1589, 1503, 1362 (SO2, 1185, 1161 (SO2, 1097, 1028; 1H NMR (500 MHz, DMSO-d6) δ 8.15 d, J
    • 2S: C, 42.38; H, 3.23; N, 22.46. Found: C, 42.69; H, 3.39; N, 22.23.
  • 24
    • 61349129862 scopus 로고    scopus 로고
    • The authors would like to thank a reviewer for suggesting the inclusion of this example
    • The authors would like to thank a reviewer for suggesting the inclusion of this example.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.