Aniline → N-[5-(3-Bromo-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide
Reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])=[CH:4][C:3]=1[Br:18].[S:19](Cl)(Cl)(=[O:21])=[O:20].N[C:25]1C=CC=CC=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].BrCC(O)=O>O1CCOCC1.O>[Br:18][C:3]1[CH:4]=[C:5]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])[CH:6]=[CH:7][C:2]=1[S:19]([CH3:25])(=[O:21])=[O:20]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
N-[5-(4-amino-3-bromo-phenyl)-4-methyl-thiazol-2-yl]acetamide (Example 7a) (1.0 g, 3.07 mmol) is converted into the corresponding sulfonyl chloride by the procedure described for the conversion of aniline (Example 1a) to sulfonyl chloride (Example 3a). A sample of this crude sulfonyl chloride (1.0 g, 2.4 mmol) is dissolved in dioxane (5 ml) and the resulting solution is added to a stirred solution of sodium sulfite (0.615 g, 4.9 mmol) and sodium hydrogen carbonate (0.41 g, 4.9 mmol) in water (5 ml) at 75° C. After 1 hour at 75° C. bromoacetic acid (0.679 g, 4.9 mmol) is added. The reaction is stirred for an additional 6 hours at 75° C. When cool the mixture is diluted with water (200 ml) and extracted with dichloromethane (3×100 ml). The combined organic extracts are washed with brine (100 ml, dried (MgSO4) and the solvent removed. Purification by chromatography on silica (EtOAc) affords the title compound.
Workup
- temperatureWhen cool the mixture
- extractionextracted with dichloromethane (3×100 ml)
- washThe combined organic extracts are washed with brine (100 ml
- dry with materialdried (MgSO4)
- customthe solvent removed
- customPurification by chromatography on silica (EtOAc)
Sources & evidence
- ORD record
- ord-4e0373189d0142afaae4785ffd54df78
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129541B2
Reaction notes
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