4-(Bromoacetyl)benzonitrile → HCID 59828836, Verbindung

HRID 1191076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191076
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](=O)[CH2:8]Br)=[CH:5][CH:4]=1)#[N:2].[F:13][C:14]([F:21])([F:20])[CH2:15][NH:16][C:17]([NH2:19])=[S:18].C(=O)(O)[O-].[Na+]>C(O)C>[F:13][C:14]([F:21])([F:20])[CH2:15][NH:16][C:17]1[S:18][CH:8]=[C:7]([C:6]2[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:19]=1

Komponenten

5

Edukt 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 516892Sodium BicarbonateHCID 202028121-(2,2,2-Trifluoroethyl)thiourea

Produkt 1

HCID 59828836HCID 59828836, VerbindungAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Slurry 4-cyanophenacyl bromide (1.4 g, 6.3 mmol), 2,2,2-trifluoroethyl-thiourea (1.0 g, 6.3 mmol) and sodium bicarbonate (529 mg, 6.3 mmol) in absolute ethanol (30 mL). Stir the mixture at reflux for 1 h under a nitrogen atmosphere. Cool to room temperature and concentrate in vacuo. Partition the residue between DCM (100 mL) and water (20 mL). Dry the organic layer over Na2SO4 and concentrate in vacuo to obtain the desired intermediate (1.7 g, 95%). MS (ES+) m/z: 284 (M+H)+.

Aufarbeitung

  1. temperatureat reflux for 1 h under a nitrogen atmosphere
  2. concentrationconcentrate in vacuo
  3. customPartition the residue between DCM (100 mL) and water (20 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. concentrationconcentrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d4a371b13503439f922b45fee5d47658
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680091B2

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