N-bromobutanimide → (5-Bromo-4-methylthiazol-2-yl)methanol
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.C1C(=O)N([Br:16])C(=O)C1>CN(C=O)C.O>[Br:16][C:6]1[S:5][C:4]([CH2:7][OH:8])=[N:3][C:2]=1[CH3:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (4-methyl-thiazol-2-yl)-methanol (7.0 g, 54.3 mmol) in DMF (80 mL) was added NBS (10.6 mg, 59.6 mmol), and the mixture was stirred at 50° C. overnight. TLC (petroleum ether:EtOAc 2:1) indicated the reaction was completed. The mixture was diluted with H2O (50 mL) and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (50 mL×3), dried over sodium sulfate, and concentrated in vacuum to give the residue which was purified by a silica gel column (petroleum ether:EtOAc 10:1) to give the title compound (11.2 g, 99%) as a brown solid.
Workup
- extractionextracted with EtOAc (50 mL×3)
- washThe combined organic layers were washed with brine (50 mL×3)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuum
- customto give the residue which
- customwas purified by a silica gel column (petroleum ether:EtOAc 10:1)
Sources & evidence
- ORD record
- ord-418e16b1fee84099b963ee8b5c57fa3a
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916593B2
Reaction notes
Loading…