Methanesulfonyl chloride → Ethyl 2-[(3-fluoro-2-[(methylsulfonyl)oxy]-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate

HRID 1188958Notes

Reaction equation

HRID 1188958 reaction equation
[F:1][C:2]1[C:3]([OH:28])=[C:4]([NH:19][N:20]=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>N1C=CC=CC=1>[F:1][C:2]1[C:3]([O:28][S:30]([CH3:29])(=[O:32])=[O:31])=[C:4]([NH:19][N:20]=[C:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 76710732Ethyl 2-[(3-fluoro-2-hydroxy-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate

Product 1

HCID 76710726Ethyl 2-[(3-fluoro-2-[(methylsulfonyl)oxy]-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoateYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cooled and stirred solution of ethyl 2-[(3-fluoro-2-hydroxy-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (4.95 g) in pyridine (50 mL) was added methanesulfonyl chloride (1.1 mL), and the mixture was stirred at 4° C. to room temperature for 15 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed successively with aqueous citric acid solution and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residual light brown solid was washed with ethyl acetate-hexane to give the title compound (5.4 g, 92%) as a pale brown solid. MS 490 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and aqueous citric acid solution
  3. washThe organic layer was washed successively with aqueous citric acid solution and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residual light brown solid was washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-4ed2d3a9214746ffb59bb769b849bcdb
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

Loading…