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O-Phenylenediamine → 1-(4-Cyano-phenyl)-3-[-(1-phenyl-ethylamino)-phenyl]-urea

HRID 49016
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49016
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1)#[N:25]>CN(C)C=O>[C:24]([C:26]1[CH:27]=[CH:28][C:29]([NH:32][C:33]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])=[O:34])=[CH:30][CH:31]=1)#[N:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 11454(1-Bromoethyl)benzeneHCID 1703804-Cyanophenyl isocyanate

Produkt 1

HCID 120439691-(4-Cyano-phenyl)-3-[-(1-phenyl-ethylamino)-phenyl]-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

1.16 g (10.8 mmol) 1,2-phenylene diamine was dissolved in 10 ml dimethyl formamide, 2.1 g (15 mmol) potassium carbonate and 1.47 ml (10.8 mmol) 1-bromo-1-phenylethane were added with stirring. After 8 hours (h) at rt, most of the starting materials were consumed. Potassium bromide was filtered off, the solvent removed, the mixture redissolved in 20 ml THF and then 1,15 g (8 mmol) 4-cyanophenylisocyanate were slowly added and stirred for another 50 h at rt. The mixture was worked up by filtration, evaporated to dryness, dissolved in ethyl acetate and washed with diluted HCl, sodium carbonate solution and brine.

Aufarbeitung

  1. custommost of the starting materials were consumed
  2. filtrationPotassium bromide was filtered off
  3. customthe solvent removed
  4. dissolutionthe mixture redissolved in 20 ml THF
  5. stirringstirred for another 50 h at rt
  6. filtrationThe mixture was worked up by filtration
  7. customevaporated to dryness
  8. dissolutiondissolved in ethyl acetate
  9. washwashed with diluted HCl, sodium carbonate solution and brine

Quellen und Nachweise

ORD-Eintrag
ord-76d8bb49b18e460c92fe6379f655d37e
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06706715B2

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