Hydrogen Bromide → N-[2-(4-Carbomethoxymethoxyphenyl)ethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

HRID 477124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477124
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH:13]([C:17]3[N:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[S:20][CH:21]=3)[CH2:12]2)=[CH:5][CH:4]=1.Br.C(=O)([O-])[O-].[K+].[K+].BrC[C:35]([O:37][CH3:38])=[O:36]>CC(C)=O>[C:35]([CH2:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH:13]([C:17]3[N:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[S:20][CH:21]=3)[CH2:12]2)=[CH:5][CH:4]=1)([O:37][CH3:38])=[O:36]

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19974138HCID 19974138, Verbindung

Produkt 1

HCID 19974221N-[2-(4-Carbomethoxymethoxyphenyl)ethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

0.6 g (1.6 mmol) of N-[2-(4-Methoxyphenyl)ethyl]-2-(2-trifluoromethyl-thiazol-4-yl)morpholine are heated on a steam bath with 6 ml of 48% strength aqueous hydrobromic acid for 3 hours. The mixture is then concentrated, toluene is added, and the mixture is again evaporated to dryness. The foamy residue is boiled under reflux in 15 ml of acetone with 1.2 g (8.7 mmol) of potassium carbonate and 0.3 ml (1.65 mmol) of methyl bromoacetate for 1 hour. The mixture is then filtered, the filtrate is concentrated, and the residue is purified on a silica gel column using toluene/acetone=4:1.

Aufarbeitung

  1. concentrationThe mixture is then concentrated
  2. additiontoluene is added
  3. customthe mixture is again evaporated to dryness
  4. filtrationThe mixture is then filtered
  5. concentrationthe filtrate is concentrated
  6. customthe residue is purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-9216375e380c40f2aa873a4a073e910a
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886814

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