Triethylamine → 2-(3-Bromophenyl)N-(3-propoxybenzyl)acetamide

HRID 1371975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371975
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH2:9])[CH2:2][CH3:3].[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21](Cl)=[O:22])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>ClCCl.[Cl-].[Na+].O>[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([NH:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=2)=[O:22])[CH:17]=[CH:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7139476(3-Propoxyphenyl)methanamineHCID 13486899(3-Bromophenyl)acetyl chloride

Produkt 1

HCID 210714132-(3-Bromophenyl)N-(3-propoxybenzyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Combine 3-propoxy-benzylamine in 50 mL of dichloromethane and add dropwise to a mixture of 3-bromophenylacetyl chloride (4.90 gm; 21.0 mmol) and triethylamine (3.60 gm; 35.9 mmol) in 250 mL of dichloromethane at 0° C. Allow the reaction to warm to room temperature and stir for 18 h. Pour the reaction into 100 mL of saturated brine, separate the layers and extract the aqueous layer with 100 mL of dichloromethane. Combine organic layers, wash with brine, dry (MgSO4), and concentrate. Purification by chromatography on silica gel with 40% EtOAc in hexanes gives the title compound.

Aufarbeitung

  1. customthe reaction
  2. additionPour
  3. customseparate the layers
  4. extractionextract the aqueous layer with 100 mL of dichloromethane
  5. washCombine organic layers, wash with brine
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate
  8. customPurification by chromatography on silica gel with 40% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2b6bc4bdd65b4be4a1bfd1a6690793cb
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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