N-bromobutanimide → Methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate
Reaktionsgleichung
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][C:7]1[CH:8]=[C:9]([C:12]2[S:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][Cl:1]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A solution of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate ax60 (2 g, 6.15 mmol, 1 eq) in acetonitrile (50 ml) is treated with a solution of N-bromosuccinimide (1.8 g, 10 mmol, 1.5 eq) in acetonitrile (10 ml) and the resulting solution is stirred 2 h at room temperature and 2 h at 60° C. After cooling, the mixture is concentrated to dryness. The residue is taken up with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Purification of the residue over silicagel (eluent: dichloromethane/benzine) affords 0.6 g of methyl 2-[3-bromo-4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i91.
Aufarbeitung
- temperatureAfter cooling
- concentrationthe mixture is concentrated to dryness
- washwashed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customPurification of the residue over silicagel (eluent: dichloromethane/benzine)
Quellen und Nachweise
- ORD-Eintrag
- ord-c1f7d4a7954c4507ac4cf1102712b33f
- Quelldatensatz
- uspto-grants-2010_09
- Patentnummer
- US07790720B2
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