Methanesulfonyl chloride → N-(4-Bromo-phenyl)-4-(4-methanesulfonylamino-phenylsulfanyl)-3-nitro-benzamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[O:14])=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:23]=[CH:24][C:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:3][CH:4]=3)=[C:10]([N+:25]([O-:27])=[O:26])[CH:11]=2)=[CH:17][CH:18]=1Participants
4
Procedure
The product of Example 13A (200 mg, 0.4501 mmol) was dissolved in anhydrous pyridine (4 mL) under a nitrogen atmosphere, treated with methanesulfonyl chloride (0.084 mL, 1.080 mmol), and stirred at room temperature for 19 hours. The solvent was removed by rotary evaporation under vacuum, and the residue dissolved in methylene chloride (100 mL) and washed with 1N aqueous hydrochloric acid (2×50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford the title compound as a yellow solid (233 mg, 99%).
Workup
- customThe solvent was removed by rotary evaporation under vacuum
- dissolutionthe residue dissolved in methylene chloride (100 mL)
- washwashed with 1N aqueous hydrochloric acid (2×50 mL)
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-bbd6e4a2f144419d9d3c3af5efa2fc83
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910595B2
Reaction notes
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