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m-Aminoacetanilide → N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide

HRID 2120916
ノート
印刷プレビュー

反応式

HRID 2120916 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[NH2:9][C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=1.[O:20]=[C:21]1[C:33]2[CH:32]=[C:31]([S:34](Cl)(=[O:36])=[O:35])[CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][C:24]([S:38](Cl)(=[O:40])=[O:39])=[CH:25][CH:26]=2>N1C=CC=CC=1>[OH:8][C:4]1[CH:3]=[C:2]([NH:1][S:34]([C:31]2[CH:32]=[C:33]3[C:28]([C:27]4[CH:26]=[CH:25][C:24]([S:38]([NH:9][C:10]5[CH:11]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:13]=[CH:14][CH:15]=5)(=[O:39])=[O:40])=[CH:23][C:22]=4[C:21]3=[O:20])=[CH:29][CH:30]=2)(=[O:35])=[O:36])[CH:7]=[CH:6][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7604m-AminoacetanilideHCID 115683-AminophenolHCID 27945729-Oxo-9H-fluorene-2,7-disulfonyl dichloride

生成物 1

HCID 9985345N-(3-{[(7-{[(3-Hydroxyphenyl)amino]sulfonyl}-9-oxo-9H-fluoren-2-yl)sulfonyl]amino}phenyl)acetamide収率 39%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

3-Aminophenol (0.29 g, 2.65 mmmol) and N-(3-aminophenyl)acetamide (0.49 g, 2.65 mmol) in pyridine were treated with 9-oxo-9H-fluorene-2,7-disulfonyl dichloride (1.00 g, 2.65 mmol) in one portion at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour after which the volatiles were evaporated under reduced pressure. The residue was partitioned between ethyl acetate and H2O. The separated organic phase was washed with 1N HCl, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (85% ethyl acetate/hexanes) to provide the title compound as a yellow solid (577 mg, 39% yield). 1H NMR (300 MHz, DMSO-d6) δ 9.91 (bs, 1H), 9.47 (s, 1H), 7.9-8.1 (m, 6H), 7.48 (m, 1H), 7.26 bd, 1H), 7.12 (t, 1H), 6.99 (t, 1H), 6.75 (m, 1H), 6.58 (t, 1H), 6.52 (dd, 1H), 6.42 (dd, 1H), 1.98 (s, 3H); MS (ESI) 562 (M−H)−.

後処理

  1. customwere evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and H2O
  3. washThe separated organic phase was washed with 1N HCl, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (85% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-3e2601917769433cb56db3d368e6f642
出典データセット
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06693136B1

反応ノート

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