N-bromobutanimide → 4-Thiazolecarboxylic acid, 5-amino-2-bromo-, methyl ester

HRID 1499393Notes

Reaction equation

HRID 1499393 reaction equation
[NH2:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[Br:11]N1C(=O)CCC1=O>C1COCC1>[NH2:1][C:2]1[S:6][C:5]([Br:11])=[N:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53408092Methyl 5-amino-1,3-thiazole-4-carboxylate

Product 1

HCID 748906024-Thiazolecarboxylic acid, 5-amino-2-bromo-, methyl esterYield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-amino-1,3-thiazole-4-carboxylate (J & W PharmLab, 10.0 g, 63.2 mmol) in THF (100 mL), N-bromosuccinimide (12.0 g, 67.4 mmol) was added portion-wise. After stirring at room temperature for 1 h, the mixture reaction was filtered to give a first crop of product as a pink solid (9.8 g). The filtrate was concentrated under reduced pressure. The resulting residue was triturated with EtOAc (15 mL) and filtered to give a second crop of product as a pink solid (5.0 g, total yield: 99%). LCMS calc. for C5H6BrN2O2S (M+H)+: m/z=236.9. found 237.0.

Workup

  1. customthe mixture reaction
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-83bbfef91f2a4eac95f7d428026ac63c
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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