N-bromobutanimide → Ethyl 2-(bromomethyl)thiazole-5-carboxylate

HRID 1739470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739470
[CH3:1][C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[S:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 21840919Ethyl 2-(bromomethyl)thiazole-5-carboxylateAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-methyl-5-thiazole carboxylate [S. H Mashragui, P. M. Keehn, JACS 104 4461-4465 (1982)] (4.73 g, 27.68 mmol) in carbon tetrachloride (30 ml) was treated with N-bromosuccinimide (4.92 g, 27.64 mmol) and benzoyl peroxide (0.03 g). The reaction mixture was heated to reflux under a strong light for 11/4 hours. The reaction was allowed to cool to ambient temperature and filtered. The filtrate was evaporated and subjected to chromatography (CH2Cl2) to give the title product (1.16 g, 17%). NMR (200 MH2,DMSO-d6) : δ8.4 (s, 1H) , 5.06 (s, 2H) , 4.33 (g, 2H), 1.3 (t, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under a strong light for 11/4 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1ea5a49c476f49608518b6a74b51d657
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965741

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