Hydrochloric Acid → HCID 178485344, Verbindung

HRID 1848621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848621
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]#[N:20])[CH3:8])=[O:6].[N:25]([Sn](CCCC)(CCCC)CCCC)=[N+:26]=[N-:27].C([Al](CC)CC)C.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[C:5]([N:7]([CH3:8])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]1[NH:27][N:26]=[N:25][N:20]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 16682930TriethylaluminumHCID 686031543-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide

Produkt 1

HCID 178485344HCID 178485344, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-bromo-4-chloro-N-[2-(3-cyano-propoxy)-phenyl]-N-methyl-benzamide (2.0 g, 4.9 mmol), azidotributyltin (4.03 mL, 14.7 mmol) and triethylaluminum (7.74 mL, 14.7 mmol, 25% in toluene) in toluene (25 mL) was heated at 80° C. for 5 hrs. The mixture was allowed to cool to room temperature and was acidified with 1N HCl. The mixture was extracted with DCM. The organic layer was washed with water and brine, and was dried. The filtrate was concentrated in vacuo and the residue purified by silica gel column chromatography (eluent: 3% MeOH in DCM) to afford 3-bromo-4-chloro-N-methyl-N-{2-[3-(1H-tetrazol-5-yl)-propoxy]-phenyl}-benzamide (1.93 g). MS [M+H]+: 451.9; tR=2.26 min. (method 1)

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with DCM
  3. washThe organic layer was washed with water and brine
  4. customwas dried
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by silica gel column chromatography (eluent: 3% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-22e89914f5d74aca87624649294b353c
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952161B2

Notizen zur Reaktion

Wird geladen…