Hydrochloric Acid → 2-Chloro-4-bromoacetyl-thiazole

HRID 1587896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587896
N[C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:10])[CH2:8][Br:9])[N:6]=1.N([O-])=O.[Na+].[ClH:15]>O.[Cu]Cl>[Cl:15][C:2]1[S:3][CH:4]=[C:5]([C:7](=[O:10])[CH2:8][Br:9])[N:6]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric Acid2×HCID 136062401-(2-Aminothiazol-4-yl)-2-bromoethanoneHCID 23668193Sodium Nitrite

Produkt 1

HCID 143477622-Chloro-4-bromoacetyl-thiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

7.6 g (6.0344 mol) of 2-Amino-4-bromoacetyl-thiazole are dissolved in 20 ml of water and 50 ml of concentrated hydrochloric acid. Now, at 0° C. and with stirring, a solution of 3.44 g (0.0499 mol) of sodium nitrite in 15 ml of water is added dropwise. The resulting diazonium salt solution is then introduced in portions into a vigorously stirred cold solution of 4.93 g (0.0449 mol) of copper(I) chloride in 15 ml of concentrated hydrochloric acid, and the mixture is stirred at room temperature for 20 hours. It is then diluted with 100 ml of water and extracted with ether. The ether extract is dried over sodium sulphate and evaporated. For purification, the crude product is purified on a silica gel column using methylene chloride as the eluant.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 20 hours
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over sodium sulphate
  5. customevaporated
  6. customFor purification
  7. customthe crude product is purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-6d18ddc9685e4013ad65e3157caf5498
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219852

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