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4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate → ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

HRID 1641059
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641059
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[C:8]([C:11]3[S:12][C:13]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)[CH:9]=[CH:10][C:2]1=2.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][C:42](=O)[O:43]C1C=CC([N+]([O-])=O)=CC=1>C(#N)C>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][C:42]([N:4]1[CH2:5][CH2:6][O:1][C:2]2[CH:10]=[CH:9][C:8]([C:11]3[S:12][C:13]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)=[CH:7][C:3]1=2)=[O:43]
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Komponenten

4

Edukt 2

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateHCID 59418724ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

Produkt 1

HCID 59418665ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylateAusbeute 310,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20B) (0.150 g, 0.34 mmol) and 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) (0.349 g, 0.11 mmol) was added acetonitrile (10 mL). The reaction mixture was allowed to heat to 85° C. and stirred for 8 hours. Then the reaction mixture was allowed to heat at 70° C. and stirred overnight. The reaction mixture was allowed to cool to rt and concentrated under reduced pressure. To the concentrate was added EtOAc and water and filtered. The layers of the filtrate were separated and extracted with EtOAc. The combined organic extracts were washed sequentially with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide 0.21 g (quantitative) ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20C): LC/MS (APCI): m/z 616.3 (M+H).

Aufarbeitung

  1. temperatureto heat at 70° C.
  2. stirringstirred overnight
  3. temperatureto cool to rt
  4. concentrationconcentrated under reduced pressure
  5. additionTo the concentrate was added EtOAc and water
  6. filtrationfiltered
  7. customThe layers of the filtrate were separated
  8. extractionextracted with EtOAc
  9. washThe combined organic extracts were washed sequentially with water, brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-927e8a0dc1d348aaa0028860dcc86a98
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114893B2

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