1,2-Dichloro-3-isocyanatobenzene → N-(4-tert-butylpyridyl)-N'-(2,3-dichlorophenyl)urea

HRID 2222316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222316
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[N:20]=[C:21]=[O:22]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:21]([NH:20][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=2[Cl:12])=[O:22])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Komponenten

5

Edukt 2

HCID 330501,2-Dichloro-3-isocyanatobenzeneHCID 123519414-(tert-Butyl)pyridin-2-amine

Produkt 1

HCID 9967659N-(4-tert-butylpyridyl)-N'-(2,3-dichlorophenyl)ureaAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-amino-4-tert-butylpyridine (192 mg) and 2,3-dichlorophenyl isocyanate (240 mg) in anh. toluene (15 mL) was heated at 70° C. under argon for 24 h. The resulting mixture was diluted with EtOAc (200 mL) then washed with water (125 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to give a gum. Trituration of the gum with hexanes afforded N-(4-tert-butylpyridyl)-N′-(2,3-dichlorophenyl) urea as a white solid (394 mg, 91%): TLC (2:1 hexanes/ethyl acetate) Rf 0.40; FAB-MS m/z 338 ((M+H)+). B2a. Reaction of a Heterocyclic Amine with N,N′-Carbonyldiimidazole Followed By Reaction with a Substituted Aniline

Aufarbeitung

  1. washthen washed with water (125 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a gum

Quellen und Nachweise

ORD-Eintrag
ord-4778195821734c868f2f043f6dabd051
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371763B2

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