Methanesulfonyl chloride → N-(4-Bromo-phenyl)-4-(4-methanesulfonylamino-phenoxy)-3-nitro-benzamide

HRID 605137Notes

Reaction equation

HRID 605137 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:22]=[CH:21][C:10]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=3)=[O:12])=[CH:9][C:8]=2[N+:23]([O-:25])=[O:24])=[CH:4][CH:3]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:21]=[CH:22][C:7]([O:6][C:5]3[CH:26]=[CH:27][C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:3][CH:4]=3)=[C:8]([N+:23]([O-:25])=[O:24])[CH:9]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 670405064-(4-Amino-phenoxy)-N-(4-bromo-phenyl)-3-nitro-benzamide

Product 1

HCID 67040270N-(4-Bromo-phenyl)-4-(4-methanesulfonylamino-phenoxy)-3-nitro-benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product of Example 91A (195 mg, 0.4554 mmol) was dissolved in anhydrous pyridine (5 mL) under a nitrogen atmosphere, treated with methanesulfonyl chloride (0.106 mL, 1.366 mmol), and stirred at room temperature for 19 hours. The solvent was removed by rotary evaporation under vacuum, and the residue dissolved in ethyl acetate (100 mL) and washed with 1N aqueous hydrochloric acid (2×50 mL), water (50 mL), and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford the title compound as a light orange solid (225 mg, 98%).

Workup

  1. customThe solvent was removed by rotary evaporation under vacuum
  2. dissolutionthe residue dissolved in ethyl acetate (100 mL)
  3. washwashed with 1N aqueous hydrochloric acid (2×50 mL), water (50 mL), and brine (50 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c1b7e65a36264ca481051e287f2437ae
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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