Chloride → 2'-(N-t-Butylsulfamoyl)-4-methylbiphenyl

HRID 257553

반응식

HRID 257553 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([Sn](C)(C)C)=[CH:18][CH:17]=1.[Cl-]>CN(C)C=O>[C:12]([NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:10])=[O:9])([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 312ChlorideHCID 617834Stannane, trimethyl(4-methylphenyl)-HCID 48250142-bromo-N-tert-butylbenzenesulfonamide

생성물 1

HCID 152820992'-(N-t-Butylsulfamoyl)-4-methylbiphenyl수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

2-Bromo-N-(tert-butyl)benzenesulfonamide (from Step B) (1.00 g, 3.92 mmol), p-tolyltrimethyltin (from Step C) (1.95 g, 6.67 mmol), bis(triphenylphosphinepalladium(II) chloride (Aldrich) (165 mg, 0.235 mmol) and dimethylformamide (25 ml) were heated with stirring under nitrogen at 90° C. for 5 hours. The black suspension was cooled to room temperature, then filtered through a pad of Celite which was washed with tetrahydrofuran. The colorless filtrate was evaporated to dryness, then chromatographed (silica gel, 10% ethyl acetate-hexane) to give the title compound (0.88 g, 74%) as a white solid; 1H NMR (300 MHz, CDCl3) δ8.16 (d, J=7.9 Hz, 1H), 7.60-7.37 (m, 4H), 7.36-7.24 (m, 3H), 3.57 (s, 1H), 2.42 (s, 3H), 0.99 (s, 9H).

후처리

  1. temperatureThe black suspension was cooled to room temperature
  2. filtrationfiltered through a pad of Celite which
  3. washwas washed with tetrahydrofuran
  4. customThe colorless filtrate was evaporated to dryness
  5. customchromatographed (silica gel, 10% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-96b8bbb5fb2546eea284fbd01e5920c3
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262412

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