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Water → HCID 13655816, Verbindung

HRID 2076422
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2076422
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](O)=[O:15])[CH:5]=[CH:4][C:3]1=2.CN(C=O)C.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.O>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 12082Methyl 4-aminobenzoateHCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Produkt 1

HCID 13655816HCID 13655816, VerbindungAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 24386Thionyl ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (0.20 g, 0.86 mmol) was dissolved in SOCl2 (4.3 mL) at 0° C. A drop of DMF was added and the mixture was stirred for 0.5 h. The SOCl2 was removed under vacuum and the crude acid chloride was dissolved in pyridine (10 mL). Methyl 4-aminobenzoate (0.143 g, 0.947 mmol) and DMAP (0.010 mg, 0.086 mmol) were added and the mixture was heated at 60° C. for 2 h with stirring. The mixture was poured into H2O and the product was extracted with EtOAc; The organic layer was washed successively with HCl (2M), saturated NaHCO3, saturated NaCl, dried over MgSO4, filtrated to give after evaporation methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate 3 (0.23 g, 73% yield) as a white solid.

Aufarbeitung

  1. customThe SOCl2 was removed under vacuum
  2. dissolutionthe crude acid chloride was dissolved in pyridine (10 mL)
  3. stirringwith stirring
  4. extractionthe product was extracted with EtOAc
  5. washThe organic layer was washed successively with HCl (2M), saturated NaHCO3, saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltrated
  8. customto give

Quellen und Nachweise

ORD-Eintrag
ord-c82adf03a25343eb88621a45518e8484
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07923579B2

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