N,N-Dimethylaniline → HCID 86603517, Verbindung

HRID 2214335

Reaktionsgleichung

Reaktionsgleichung von HRID 2214335
[C:1]([O:8][CH2:9][C:10]1([CH3:25])[CH2:14][N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([C:21](Cl)=[O:22])[C:11]1=[O:24])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:26][NH:27][C:28]1[CH:70]=[CH:69][CH:68]=[CH:67][C:29]=1[C:30]([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([OH:43])=[C:35]([C:44](=[O:66])[NH:45][C:46]2[CH:51]=[C:50]([CH3:52])[CH:49]=[CH:48][C:47]=2[O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH:34]=1)=[O:31].CN(C)C1C=CC=CC=1.[O:80]1CCCC1>>[C:1]([O:8][CH2:9][C:10]1([CH3:25])[C:11](=[O:24])[N:12]([C:21]([N:27]([CH3:26])[C:28]2[CH:70]=[CH:69][CH:68]=[CH:67][C:29]=2[C:30]([O:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]([OH:43])=[C:35]([C:44](=[O:66])[NH:45][C:46]3[CH:51]=[C:50]([CH3:52])[CH:49]=[CH:48][C:47]=3[O:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH:34]=2)=[O:31])=[O:22])[N:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:14]1=[O:80])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 4

HCID 949N,N-DimethylanilineHCID 8028Tetrahydrofuran2×HCID 695897322-Methylamino-benzoic acid 3-(2-dodecyloxy-5-methyl-phenylcarbamoyl)-4-hydroxy-naphthalen-1-yl esterHCID 86603516HCID 86603516, Verbindung

Produkt 1

HCID 86603517HCID 86603517, Verbindung

Versuchsvorschrift

Hexanoic acid, 2-chlorocarbonyl-4-methyl-3-oxo-1-phenyl-pyrazolidin-4-ylmethyl ester (0.80 g, 0.0022 mol) was dissolved in tetrahydrofuran (10 ml) and added to a stirred solution of 2-methylamino-benzoic acid, 3-(2-dodecyloxy-5-methyl-phenylcarbamoyl)-4-hydroxy-naphthalen-1-yl ester [A] (1.28 g, 0.0021 mol) and N,N-dimethylaniline (0.28 g, 0.0023 mol) in dry tetrahydrofuran (5 ml) and the solution stirred for 72 hr under argon atmosphere in a flask equipped with a reflux condenser to limit evaporation. The reaction mixture was evaporated, re-dissolved in ethyl acetate (300 ml) and washed with 2 M aqueous hydrochloric acid (150 ml) followed by water (20 ml). The organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated to give a yellow-brown oil which contained product and starting amine. The oil was chromatographed on a Flashpak Si 50 g column eluting with hexane/ethyl acetate (4:1->2:1). The higher running components were discarded. The more polar component was evaporated to give pale yellow viscous oil. Analysis was consistent with the desired product. The total yield of product was 1.3 g (62%).

Aufarbeitung

  1. customequipped with a reflux condenser
  2. customevaporation
  3. customThe reaction mixture was evaporated
  4. dissolutionre-dissolved in ethyl acetate (300 ml)
  5. washwashed with 2 M aqueous hydrochloric acid (150 ml)
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give a yellow-brown oil which
  11. customThe oil was chromatographed on a Flashpak Si 50 g column
  12. washeluting with hexane/ethyl acetate (4:1->2:1)
  13. customThe more polar component was evaporated
  14. customto give pale yellow viscous oil

Quellen und Nachweise

ORD-Eintrag
ord-70e54ae7bcfc4807a0ae73ec9e869628
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07108964B2

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