Fluorine → p-Tolyl-N-fluoro-N-neopentylsulfonamide

HRID 1633206

반응식

HRID 1633206 반응식
[CH2:1]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[C:2]([CH3:5])([CH3:4])[CH3:3].[F:17]F>C(=O)(O)[O-].[K+]>[F:17][N:6]([CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:8])=[O:9]

참가 물질

4

반응물 2

HCID 24524FluorineHCID 13222555N-(2,2-Dimethylpropyl)-4-methylbenzene-1-sulfonamide

생성물 1

HCID 145159p-Tolyl-N-fluoro-N-neopentylsulfonamide수율 57%

시약·촉매·용매 1

HCID 516893Potassium Bicarbonate용매

실험 절차

N-Neopentyl-p-toluenesulfonamide (2.41 g, 10 mmole) was dissolved in 1:1 fluorotrichloromethanechloroform (450 mL) and the solution was cooled to -78° under nitrogen. Fluorine (approximately 15 mmole, 5% in nitrogen) was bubbled into the solution through a vibrating mixer shaft for 2 h. The cold reaction mixture was poured into aqueous 10% potassium bicarbonate solution (200 mL) and the layers were separated. The organic phase was washed with aqueous 10% sodium thiosulfate (200 mL) and saturated sodium chloride (200 mL) solutions and dried over anhydrous magnesium sulfate. Filtration and removal of solvent under reduced pressure left a solid. Purification of the solid by flash column chromatography (silica, 25% methylene chloride in hexane) yielded N-fluoro-N-neopentyl-p-toluene-sulfonamide as a solid (1.47 g, 57% yield). This material, and additional samples prepared by this procedure, were analyzed and provided the following results: mp 58°-62.5°; IR (KBr) γmax (cm-1) 3440 (b), 2980 (w), 1370 (m), 1175 (s), 734 (m); 1H NMR (80 MHz, CDCl3) δ1.00 (s, 9H, C(CH3)3), 2.50 (s, 3H, CH3), 3.00 (d, J=44 Hz, 2H, NCH2), 7.40 (d, J=8 Hz, 2H, aromatic), 7.83 (d, J=8 Hz, 2H, aromatic); 19F NMR (94.1 MHz, CDCl3) -36.88 (t, J=44 Hz, 1F, NF); HRMS calcd. for C12H18NO2SF: 259.1042; found: 259.1029.

후처리

  1. temperaturethe solution was cooled to -78° under nitrogen
  2. customThe cold reaction mixture
  3. customthe layers were separated
  4. washThe organic phase was washed with aqueous 10% sodium thiosulfate (200 mL) and saturated sodium chloride (200 mL) solutions
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration and removal of solvent under reduced pressure
  7. waitleft a solid
  8. customPurification of the solid by flash column chromatography (silica, 25% methylene chloride in hexane)

출처 및 근거

ORD 기록
ord-48bb6a307a024ae78526eb79c9daf159
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04479901

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