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

HRID 1268892Notes

Reaction equation

HRID 1268892 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1

Participants

4

Reactant 2

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

Product 1

HCID 21840919Ethyl 2-(bromomethyl)thiazole-5-carboxylateYield 41.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (0.91 g, 5.1 mmol) was added to a solution of ethyl 2-methyl-thiazole-5-carboxylate (0.8 g, 4.7 mmol) in carbon tetrachloride. The resultant reaction mixture was stirred for one hour whilist being illuminated by a photoflood lamp. After removing the solvent from the reaction mixture the resultant material was partitioned between ethyl acetate and water. The organic phase was then separated off, dried (MgSO4) and the evaporated. Chromatography on silica, eluting with 30% ethyl acetate in hexane, gave ethyl 2-(bromomethyl)-1,3-thiazole-5-carboxylate (490 mgs), NMR: δH (300 MHz, DMSO-d6, 1.20–1.38 (3 H,t); 4.20–4.37 (2 H,q); 5.05 (2 H, s); 8.55 (1 H, s).

Workup

  1. customThe resultant reaction mixture
  2. customwhilist being illuminated by a photoflood lamp
  3. customAfter removing the solvent from the reaction mixture the resultant material
  4. customwas partitioned between ethyl acetate and water
  5. customThe organic phase was then separated off
  6. dry with materialdried (MgSO4)
  7. washChromatography on silica, eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4daf22f70f514f42823ad518173ab37b
Source dataset
uspto-grants-2007_04
Patent number
US07199140B2

Reaction notes

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