N-bromobutanimide → HCID 67465550, compound

HRID 1406300Notes

Reaction equation

HRID 1406300 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:7]([OH:9])[CH3:8])[S:5][CH:6]=1.C1C(=O)N([Br:17])C(=O)C1>CN(C=O)C.O>[Br:17][C:6]1[S:5][C:4]([CH:7]([OH:9])[CH3:8])=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 154448277586-99-4

Product 1

HCID 67465550HCID 67465550, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-methylthiazol-2-yl)ethanol of preparation 95 (3.3 g, 22.9 mmol) in DMF (80 mL) was added NBS (4.47 g, 25.2 mmol), and the mixture was stirred at 50° C. for 2 hours. TLC (petroleum ether:EtOAc 3:1) indicated the reaction was completed. The mixture was diluted with H2O (100 mL) and extracted with EtOAc (80 mL×3). The combined organic extracts were washed with brine (80 mL×3), dried over sodium sulfate, and concentrated in vacuum to give the residue which was purified by a silica gel column eluting with petroleum ether:EtOAc=25:1-5:1 to give the title compound as a yellow solid (3.7 g, 74%).

Workup

  1. extractionextracted with EtOAc (80 mL×3)
  2. washThe combined organic extracts were washed with brine (80 mL×3)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customto give the residue which
  6. customwas purified by a silica gel column
  7. washeluting with petroleum ether

Sources & evidence

ORD record
ord-4ee6e6b5f43843829184e8ce6465e844
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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