2-Chlorobenzoyl isocyanate → 6-{2,6-Dichloro-4-[(2-chlorobenzoyl)ureido]phenoxy}hexanoic acid

HRID 1634251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634251
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[NH2:13][C:14]1[CH:28]=[C:27]([Cl:29])[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:16]([Cl:30])[CH:15]=1>C(#N)C>[Cl:29][C:27]1[CH:28]=[C:14]([NH:13][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=2[Cl:1])=[O:8])[CH:15]=[C:16]([Cl:30])[C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]

Komponenten

4

Edukt 2

HCID 99423112-Chlorobenzoyl isocyanateHCID 186777636-(4-Amino-2,6-dichlorophenoxy)hexanoic acid

Produkt 1

HCID 120427646-{2,6-Dichloro-4-[(2-chlorobenzoyl)ureido]phenoxy}hexanoic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A solution of 7.5 g (41.1 mmol) of 2-chlorobenzoyl isocyanate in 300 ml of acetonitrile was added to a suspension of 10.0 g (34.2 mmol) of 6-(4-amino-2,6-dichlorophenoxy)hexanoic acid in 700 ml of dry acetonitrile under a protective gas atmosphere at room temperature. The mixture was boiled under reflux for 2 hours and cooled to room temperature. The resulting precipitate was filtered off with suction and washed with 50 ml of acetonitrile. The residue was stirred with 100 ml of methanol, filtered off with suction, washed with a little methanol and dried at 40° C. under vacuum overnight. 13.7 g (28.9 mmol, 85%) of the required product were obtained. Melting point: about 171-173° C.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. filtrationThe resulting precipitate was filtered off with suction
  3. washwashed with 50 ml of acetonitrile
  4. filtrationfiltered off with suction
  5. washwashed with a little methanol
  6. customdried at 40° C. under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-3c69dc8fda9f48f28ef9e0a0c5574e29
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506778B2

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