Sodium hydride → HCID 72429334, Verbindung

HRID 349609

Reaktionsgleichung

Reaktionsgleichung von HRID 349609
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[H-].[Na+].[Cl:18][CH:19]=[CH:20][CH2:21]Cl>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[N:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:21][CH:20]=[CH:19][Cl:18]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 3571360N-(tert-Butoxycarbonyl)-2-bromoaniline

Produkt 1

HCID 72429334HCID 72429334, VerbindungAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 3.2 (350 mg, 1.29 mmol) in DMF (7 ml) was cooled to 0° C. and NaH (93 mg, 3.85 mmol) was added. The resulting mixture was stirred for 15 mins and 1,3 dichloropropene (358 μl, 3.85 mmol) was added. The mixture was allowed to warm to 25 ° C. and stirred for 15 h. The mixture was then concentrated. H2O (10 ml) was added to the residue and the solution was extracted with EtOAc (3×10 ml). The combined organic layers were dried with MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9) to afford 3.3 (400 mg, 89%) as a pale yellow oil. FABMS (NBA/NaI) 346 (M+H+ expected 346).

Aufarbeitung

  1. stirringstirred for 15 h
  2. concentrationThe mixture was then concentrated
  3. additionH2O (10 ml) was added to the residue
  4. extractionthe solution was extracted with EtOAc (3×10 ml)
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-524453802d4c4ea4bede5730af445a25
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179921B2

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