N-bromobutanimide → Ethyl 5-amino-2-bromothiazole-4-carboxylate

HRID 512542Notes

Reaction equation

HRID 512542 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[N:15]=[CH:16][S:17][C:18]=1[NH2:19])=[O:13])[CH3:10]>C(#N)C.CCOC(C)=O>[NH2:19][C:18]1[S:17][C:16]([Br:1])=[N:15][C:14]=1[C:12]([O:11][CH2:9][CH3:10])=[O:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 59355801Ethyl 5-amino-2-bromothiazole-4-carboxylateYield 58.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Bromosuccinimide (0.54 g, 3.03 mmol) was added to a solution of 5-aminothiazole-4-carboxylic acid ethyl ester (0.44 g, 2.53 mmol) [prepared according to the procedure described by Golankiewicz et al. (Tetrahedron, 41 (24), 5989-5994 (1985))] in acetonitrile (10 mL), and the mixture was stirred for 30 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with 5% K2CO3 aq. solution (25 mL) followed by brine (25mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluted with 15% EtOAc in hexane to give 0.37 g (58% yield) of the titled compound.

Workup

  1. customprepared
  2. washwashed with 5% K2CO3 aq. solution (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with 15% EtOAc in hexane

Sources & evidence

ORD record
ord-939b78f90ce94b139a36b81af49567f9
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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