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Hydrochloric Acid → 4-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Benzoic Acid

HRID 1760840
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1760840
[CH2:1]([N:6]([C:21]1[CH:30]=[CH:29][C:28]2[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=2[CH:22]=1)[C:7](=[O:20])[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].C1COCC1.Cl>C(O)C.O>[CH2:1]([N:6]([C:21]1[CH:30]=[CH:29][C:28]2[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:33])([CH3:34])[C:23]=2[CH:22]=1)[C:7](=[O:20])[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 11784539HCID 11784539, Verbindung

Produkt 1

HCID 101602234-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Benzoic AcidAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of ethyl 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (37) (360 mg, 0.77 mmole) in 10 mL ethanol was treated with 430 mg of potassium hydroxide in 2 mL water. THF (2 mL) was added and the mixture was heated to 45° C. for two hours. The reaction mixture was diluted with 10 mL water, the pH adjusted to 2 with concentrated HCl and then extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by trituration in pentane and 280 mg of 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (27) were obtained as a white solid. M.P.: 184-186° C.

Aufarbeitung

  1. extractionextracted with three 25 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow solid
  6. customThe product was purified by trituration in pentane

Quellen und Nachweise

ORD-Eintrag
ord-15875df89ccc486fb9e16083cb76d2db
Quelldatensatz
uspto-grants-2005_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06844466B2

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