Hydroquinone → 4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

HRID 1939310

반응식

HRID 1939310 반응식
[F:1][C:2]([F:27])([F:26])[C:3]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][CH:10]=2)[N:5]([CH:16]2[CH2:21][CH:20]=[C:19]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:18]=[CH:17]2)[N:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(C=CC(O)=CC=1)O>O1CCOCC1>[F:27][C:2]([F:1])([F:26])[C:3]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=[CH:9][CH:10]=2)[N:5]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[N:4]=1

참가 물질

5

반응물 3

HCID 785HydroquinoneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone3회HCID 189203554,5-dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide

생성물 1

HCID 214675164-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide수율 90%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

4,5-Dihydro-4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide from Step 2 (393 mg, 1.0 mmol) was dissolved in 1,4-dioxane (50 ml), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (227 mg, 1.0 mmol) was added. The reaction was heated to reflux for 16 hours at which time a second equivalent of DDQ (227 mg, 1.0 mmol) was added and the reaction was heated to reflux for an additional 24 hours. At three successive 24 hour intervals, 1.0 mmol additional DDQ was added and heating continued until no starting material was left. The reaction was cooled to room temperature at which time most of the hydroquinone by-product precipitated. The reaction was filtered and concentrated. The residue was chromatographed on silica gel eluting with 50% ethyl acetate in hexane to yield 4-[3-(trifluoromethyl)-1H-benz[g]indazol-1-yl]benzenesulfonamide (352 mg, 90%): 1H NMR (acetone d6) δ=6.89 (broad s, 2H), 7.5 (m, 1H), 7.7 (m, 2H), 7.89 (s, 2H), 8.0 (d, 2H, j=8.7 Hz), 8.15 (d, 1H, j=8.3 Hz), 8.3 (d, 2H, j=8.7 Hz); 19F NMR (acetone d6) δ-61.7 ppm (s, 3F).

후처리

  1. temperatureThe reaction was heated
  2. additionwas added
  3. temperaturethe reaction was heated
  4. temperatureto reflux for an additional 24 hours
  5. temperatureheating
  6. waitwas left
  7. customprecipitated
  8. filtrationThe reaction was filtered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel eluting with 50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-88adc217610d497b84c9c2350ff3dd8c
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696143

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