Hydrochloric Acid → N-(3-cyanophenyl)-N'-(4-cyanophenyl)cycloheptylurea

HRID 582560

Reaktionsgleichung

Reaktionsgleichung von HRID 582560
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][CH2:27]Br.Cl.[CH3:30][CH2:31][CH2:32]CCC>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([CH:24]2[CH2:32][CH2:31][CH2:30][CH2:27][CH2:26][CH2:25]2)[C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 8058HexaneHCID 24758Sodium hydride2×HCID 3421111-(3-Cyanophenyl)-3-(4-cyanophenyl)urea

Produkt 1

HCID 53652841N-(3-cyanophenyl)-N'-(4-cyanophenyl)cycloheptylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-(3-Cyanophenyl)-N'-(4-cyanophenyl)urea (0.25 g, 0.95 mmol) was dissolved in DMF (2 ml) and added to a cooled slurry of sodium hydride (0.80 g, 2.0 mmol, hexane washed to remove the mineral oil) in dimethylformamide (25 ml) under a nitrogen atmosphere. After strirring for 15 min, 1,4-dibromobutane (0.25 g, 0.95 mmol) was added slowly. The reaction was stirred at 0° C. for 1 h and then allowed to warm to 75° C. for 3 h. To the reaction additional sodium hydride was added and the reaction was heated to 75° C. for an additional 6 h. The reaction was allowed to cool to ambient temperature, was poured into 1N HCl and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried (MgSO4) and concentrated to give a viscous oil. The oil was purified by flash chromatography on silica gel eluting with methylene chloride: ethyl acetate 95:5 to give N-(3-cyanophenyl)-N'-(4-cyanophenyl)cycloheptylurea as an oil (0.075 gm 0.24 mmol); LRMS (M+H)+ m/z 317; 1H NMR (CDCl3): 7.7-7.45(m, 6H), 7.4(d, 2H), 3.82(m, 4H), 1.95(m, 4H).

Aufarbeitung

  1. washwashed
  2. customto remove the mineral oil) in dimethylformamide (25 ml) under a nitrogen atmosphere
  3. temperatureto warm to 75° C. for 3 h
  4. temperaturethe reaction was heated to 75° C. for an additional 6 h
  5. temperatureto cool to ambient temperature
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto give a viscous oil
  11. customThe oil was purified by flash chromatography on silica gel eluting with methylene chloride: ethyl acetate 95:5

Quellen und Nachweise

ORD-Eintrag
ord-3a6819ed95b44db5abcf8c87c9a65708
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925635

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