Dimethylcarbamoyl Chloride → N'-(4-bromo-2-fluorobenzyl)-N,N-dimethylurea

HRID 500186

Reaktionsgleichung

Reaktionsgleichung von HRID 500186
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[C:10]([F:16])[CH:9]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:3](=[O:4])[N:2]([CH3:6])[CH3:1])=[C:10]([F:16])[CH:9]=1

Komponenten

6

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 3770848(4-Bromo-2-fluorophenyl)methanamine

Produkt 1

HCID 67225137N'-(4-bromo-2-fluorobenzyl)-N,N-dimethylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N,N-Dimethylcarbamoyl chloride (101 μL, 1.1 mmol) was added to a solution of 1-(4-bromo-2-fluorophenyl)methanamine (0.204 g, 1.0 mmol) and triethylamine (148.1 μL, 1.10 mmol) in methylene chloride (5 mL) at 0° C., followed by 4-dimethylaminopyridine (0.012 g, 0.1 mmol). After 10 min, the ice-water bath was removed and the mixture was stirred overnight at RT. The mixture was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue (253 mg, 91.9%) was directly used in next step without further purification. LCMS: (M+H)=276.9/274.9.

Aufarbeitung

  1. customthe ice-water bath was removed
  2. washThe mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue (253 mg, 91.9%) was directly used in next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d0bc222f51e94dbab84bdf4c99763d31
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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