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(3-Bromophenyl)acetic acid → 2-(3-Bromophenyl)acetamide

HRID 2243210
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243210
O[N:2]1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.C(=O)([O-])[O-].[NH4+].[NH4+].[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]([OH:36])=O)[CH:30]=[CH:31][CH:32]=1.Cl.CN(C)CCCN=C=NCC>>[Br:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34]([NH2:2])=[O:36])[CH:30]=[CH:31][CH:32]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 74653(3-Bromophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 117360272-(3-Bromophenyl)acetamide

Versuchsvorschrift

1-Hydroxybenzotriazole (HOBT, 13.82 g, 102.3 mmol), N-ethyldiisopropyl amine (Hunig's base, 13.22 g, 102.3 mmol) and ammonium carbonate (27.0 g, 279.0 mmol) were added to a solution of (3-bromophenyl)acetic acid (20.0 g, 93.0 mmol) in freshly dried and distilled tetrahydrofuran (80 mL) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 5 minutes and then cooled to 0° C. and stirred at the same temperature for about 1 hour. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCLHCl, 19.61 g, 102.3 mmol) was added at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 12 hours. The solvent was evaporated under vacuum and water was added. A white solid was obtained which was filtered, washed with water and dried. Yield: 12.69 g.

Aufarbeitung

  1. customin freshly dried
  2. distillationdistilled tetrahydrofuran (80 mL) under a nitrogen atmosphere
  3. temperaturecooled to 0° C.
  4. stirringstirred at the same temperature for about 1 hour
  5. stirringThe reaction mixture was stirred at room temperature for about 12 hours
  6. customThe solvent was evaporated under vacuum and water
  7. additionwas added
  8. customA white solid was obtained which
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6e7e639fb1db440782789e3a93073842
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07674811B2

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