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

HRID 1739470Notes

Reaction equation

HRID 1739470 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-1ea5a49c476f49608518b6a74b51d657
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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