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Sodium Carbonate → 4-[6-(4-Fluorophenyl)-1,3-benzodioxol-5-yl]benzenesulfonamide

HRID 1839940
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HRID 1839940 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](B(O)O)=[CH:10][C:11]3[O:15][CH2:14][O:13][C:12]=3[CH:16]=2)=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[CH:10][C:11]3[O:15][CH2:14][O:13][C:12]=3[CH:16]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 696964-BromobenzenesulfonamideHCID 23451199[6-(4-Fluorophenyl)-1,3-benzodioxol-5-yl]boronic acid

생성물 1

HCID 234511134-[6-(4-Fluorophenyl)-1,3-benzodioxol-5-yl]benzenesulfonamide수율 76%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 1140Toluene용매

실험 절차

Under nitrogen, 500 mg of Pd(PPh3)4 was added to a stirred solution of 1.55 g (6.0 mmol) of [6-(4-fluorophenyl)-1,3-benzodioxol-5-yl]boronic acid (Step 2) and 1.09 g (4.62 mmol) of 4-bromobenzenesulfonamide (Lancaster) in 30 mL of toluene, 20 mL of ethanol, and 15 mL of 2M Na2CO3. After vigorous stirring at reflux for 6 hours, the solvent was removed in vacuo and the residue dissolved in ethyl acetate. The resulting solution was washed with water and dried over Na2SO4. Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7) gave 1.3 g (76%) of 4-[6-(4-fluorophenyl)-1,3-benzodioxol-5-yl]benzenesulfonamide as a colorless solid: mp 191.0-192.5° C.; NMR (CDCl3) δ 4.80 (s, 2H), 6.06 (s, 2H), 6.83-6.92 (m, 4H), 6.97-7.06 (m, 2H), 7.20 (d, J=8.5 Hz, 2H), 7.74 (d, J=8.5 Hz, 2H). MS (FAB): m/e 372 (M+H). Anal. Calc'd for C19H14FNO4S: C, 61.45; H, 3.80; N, 3.77. Found: C, 61.48; H, 3.92; N, 3.68.

후처리

  1. temperatureat reflux for 6 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe resulting solution was washed with water
  5. dry with materialdried over Na2SO4
  6. customPurification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7)

출처 및 근거

ORD 기록
ord-9caac3372dda4830a711693321f039d0
출처 데이터셋
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06677488B2

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