Aniline → N-[5-(3-Bromo-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

HRID 2247346Notes

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

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-fa37312654b549d7b1a0dce80b06e3e4
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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