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

HRID 252276Notes

Reaction equation

HRID 252276 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][CH:10]=1)=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH2:11])[S:9][C:10]=1[Br:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 73216Ethyl 2-aminothiazole-4-carboxylate

Product 1

HCID 1284665ethyl 2-amino-5-bromothiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Amino-thiazole-4-carboxylic acid ethyl ester (1.4 g, 8 mmol) is dissolved in acetonitrile (15 ml) and N-bromosuccinimide. (1.7 g, 9.6 mmol, 1.2 equiv.) was added in one portion. The mixture was stirred at room temp. for 3 hours, then filtered and the filtrate was evaporated. After purification on silica-gel with ethyl acetate/n-heptane as eluent, 0.71 g of an off-white solid were obtained: MS: m/e 248.9 (M−H).

Workup

  1. addition(1.7 g, 9.6 mmol, 1.2 equiv.) was added in one portion
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. customAfter purification on silica-gel with ethyl acetate/n-heptane as eluent

Sources & evidence

ORD record
ord-f55f2847b102432cbcbc66f32d12bcb2
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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