Bromine → N-[5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13](=O)[CH3:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].BrBr.BrC(C1C=CC(S(C)(=O)=O)=C(F)C=1)C(=O)C.[C:34]([NH:37][C:38]([NH2:40])=[S:39])(=[O:36])[CH3:35]>O1CCOCC1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[S:39][C:38]([NH:37][C:34](=[O:36])[CH3:35])=[N:40][C:13]=2[CH3:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
1-(3-Fluoro-4-methanesulfonyl-phenyl)-propan-2-one (Example 64c) (1.0 g, 4.34 mmol) is dissolved in dioxane (35 ml) and the solution is cooled to 10° C. at which point the mixture is semi frozen. Bromine (0.067 ml, 1.2 mmol, 0.3 eq.) is added slowly and the mixture is stirred for an additional 15 min in a semi frozen state. The mixture is then allowed to warm to room temperature and the solvent is removed to give a brown oil containing starting material and 1-bromo-1-(3-fluoro-4-methanesulfonyl-phenyl)-propan-2-one. This material is dissolved in ethanol (30 ml) and N-acetylthiourea (0.369 g, 3.1 mmol) is added in one portion. The mixture is stirred at 60° C. for 30 minutes then allowed to cool whereupon the product crystallised. Filtration affords the title compound as a white solid.
Workup
- temperatureis semi frozen
- temperaturefrozen state
- temperatureto warm to room temperature
- customthe solvent is removed
- customto give a brown oil
- additioncontaining
- stirringThe mixture is stirred at 60° C. for 30 minutes
- temperatureto cool whereupon the product
- customcrystallised
- filtrationFiltration
Sources & evidence
- ORD record
- ord-5278b58cddc3400b99b9b2eeafcdee39
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129541B2
Reaction notes
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