Hydrochloric Acid → HCID 21920085, Verbindung

HRID 1244660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244660
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:23]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]=[C:37]=[O:38])=[CH:32][CH:31]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].Cl>ClCCl>[O:21]=[C:19]1[NH:18][C:17](=[O:22])[CH:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[C:37]([NH:36][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:35][CH:34]=4)=[O:38])[CH:4]=3)=[CH:14][CH:13]=2)[S:20]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 27694231-(Hexyloxy)-4-isocyanatobenzeneHCID 21920157HCID 21920157, Verbindung

Produkt 1

HCID 21920085HCID 21920085, VerbindungAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.67 g (2.14 mmol) of 5-(3′-methylaminobiphenyl-4-ylmethyl)thiazolidine-2,4-dione in 20 ml of dichloromethane is introduced into a 50 ml round-bottomed flask. 1 g (4.3 mmol) of 1-hexyloxy-4-isocyanatobenzene is added and the mixture is heated under reflux for 16 hours. The reaction medium is poured at room temperature over a 1 N HCl solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulphate. After evaporation of the solvents, the product obtained is purified by chromatography on silica gel (eluent: heptane/ethyl acetate=3/2). 0.78 g (68%) of 1-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-yl]-3-(4-hexyloxyphenyl)-1-methylurea is obtained in the form of a white powder having a melting point of 146–148° C.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customAfter evaporation of the solvents
  7. customthe product obtained
  8. customis purified by chromatography on silica gel (eluent: heptane/ethyl acetate=3/2)

Quellen und Nachweise

ORD-Eintrag
ord-1a8a7738eec945198317776372c17169
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122564B2

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