Hydrochloric Acid → HCID 178485344, Verbindung

HRID 1485976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1485976
[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-e7d96445ec854452acc743191f9a87ce
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422310B2

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