Methanesulfonyl chloride → Ethyl 2-[(2-[(methylsulfonyl)oxy]-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}phenyl)hydrazono]propanoate

HRID 1188920Notes

Reaction equation

HRID 1188920 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:19][N:20]=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].[CH3:28][S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[CH3:28][S:29]([O:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[NH:19][N:20]=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride3×HCID 86652844Ethyl 2-[(2-hydroxy-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}phenyl)hydrazono]propanoate

Product 1

HCID 86652845Ethyl 2-[(2-[(methylsulfonyl)oxy]-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}phenyl)hydrazono]propanoateYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 2-[(2-hydroxy-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}phenyl)-hydrazono]propanoate (37.7 g) in pyridine (450 mL) was added methanesulfonyl chloride (8.9 mL) at 0° C., and the mixture was stirred at room temperature for 1 h. Methanesulfonyl chloride (8.9 mL) was added to the mixture at 0° C. again, and the mixture was stirred at room temperature for 1 h. Furthermore, methanesulfonyl chloride (8.9 mL) was added to the mixture at 0° C., and the mixture was stirred at room temperature for 15 h. The mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed successively with 1M hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (37.05 g, 83%) as an off-white solid. MS 472 (MH+).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. stirringthe mixture was stirred at room temperature for 15 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
  6. washThe organic layer was washed successively with 1M hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe residual solid was washed with diethyl ether

Sources & evidence

ORD record
ord-a116653737aa4fa9ad06c5f02087ba51
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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