Acetic Acid → 1-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea

HRID 499939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499939
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[CH2:15][NH2:16].[O-:19][C:20]#[N:21].[K+].C(O)(=O)C>C1COCC1.O.C(OCC)(=O)C>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:6]=1[CH2:15][NH:16][C:20]([NH2:21])=[O:19]

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 44235013(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)phenyl)methanamine

Produkt 1

HCID 442352571-(2-(3,3-Dimethylbutyl)-4-(trifluoromethyl)benzyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of Example 1B (9.0 g, 35 mmol), potassium cyanate (4.2 g, 52 mmol), and glacial acetic acid (3.1 mL, 52 mmol) in THF (70 mL) and water (7 mL) was stirred at 60° C. for 2 hours, diluted with ethyl acetate, and sequentially washed with saturated aqueous NaHCO3 and brine. The organic layer was concentrated under reduced pressure to provide the title compound. 1H-NMR (DMSO-d6) δ 7.41 (m, 3H), 4.69 (brs, 1H), 4.45 (d, 2H), 4.37 (brs, 2H), 2.64 (ddd, 2H), 1.45 (ddd, 2H), 0.99 (s, 9H).

Aufarbeitung

  1. washsequentially washed with saturated aqueous NaHCO3 and brine
  2. concentrationThe organic layer was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4aba15091225447dad193c4ab4a5006c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767705B2

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