Water → 1-(3-Bromophenyl)-3-heptyl-1-methylurea

HRID 390662

Reaktionsgleichung

Reaktionsgleichung von HRID 390662
[CH2:1]([N:8]=[C:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Br:11][C:12]1[CH:13]=[C:14](CN)[CH:15]=[CH:16][CH:17]=1.[CH2:20]([N:22](CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[Br:11][C:12]1[CH:13]=[C:14]([N:22]([CH3:20])[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:10])[CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 138341n-Heptyl isocyanateHCID 457587Benzenemethanamine, 3-bromo-

Produkt 1

HCID 116168371-(3-Bromophenyl)-3-heptyl-1-methylureaAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3.2 mL (20 mmol) of heptyl isocyanate are added to a solution of 2.5 g (13 mmol) of (3-bromophenyl)methylamine (prepared according to Example 24f) in 10 mL of tetrahydrofuran in the presence of 2 mL of triethylamine. The reaction mixture is stirred for 12 hours at room temperature. The reaction is stopped by addition of 2 mL of water and extraction with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 3.4 g (77%) of 1-(3-bromophenyl)-3-heptyl-1-methylurea are obtained in the form of a solid.

Aufarbeitung

  1. dry with materialdried over sodium sulfate
  2. customThe solvents are evaporated off
  3. customthe residue is then purified by chromatography on a column of silica
  4. washeluted with a 70/30 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-1fe78045841c41bd8e93be2ba27e033d
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383652B2

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