Benzyl Bromide → 2-Chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole

HRID 355027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 355027
[Cl:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCCCCC.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[Cl:1][C:2]1[S:3][C:4]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 14798Sodium HydroxideHCID 12953359(2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

Produkt 1

HCID 129533662-Chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazoleAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4.34 g (0.02 mol) of the compound of Example 4, 14.1 g (0.0825 mol) of benzyl bromide, 0.1 g of Aliquat 336 (tradename of phase transfer catalyst available from the General Mills Co.) 25 ml of hexane, 15 ml of 50% sodium hydroxide, and 15 ml of water was held at reflux for 30 minutes. The hexane layer was separated, dried over MgSO4 and concentrated under reduced pressure. The residue (6.8 g) was Kugelrohr distilled at 2 mm (pot temperature 120°-130° C.) to give 5.0 g (81% yield) of 2-chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole nD25 1.5215.

Aufarbeitung

  1. temperatureat reflux for 30 minutes
  2. customThe hexane layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. distillationdistilled at 2 mm (pot temperature 120°-130° C.)

Quellen und Nachweise

ORD-Eintrag
ord-cf71c2a25c6c4ed9bdffff403d63cce2
Quelldatensatz
uspto-grants-1983_03
Patentnummer
US04377693

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