Water → HCID 86652841, compound

HRID 1188905Notes

Reaction equation

HRID 1188905 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=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].O>N1C=CC=CC=1>[CH3:28][S:29]([O:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:13][CH:14]=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

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chloride2×HCID 86652840HCID 86652840, compound

Product 1

HCID 86652841HCID 86652841, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-[(2-hydroxy-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}phenyl)hydrazono]propanoate (21.1 g) in pyridine (220 mL) was added methanesulfonyl chloride (5.0 mL) at 0° C. The mixture was stirred at 0° C. for 2 h, and then at room temperature for 16 h. The mixture was cooled to 0° C., and methanesulfonyl chloride (5.0 mL) was added to the mixture again. After stirring at room temperature for 2 h, water was added to the mixture. The mixture was extracted with ethyl acetate. 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 oil was solidified with ethyl acetate-diethyl ether, and the resulting solid was washed with diethyl ether to give the title compound (20.0 g, 79%) as a pale yellow solid. MS 472 (MH+).

Workup

  1. waitat room temperature for 16 h
  2. temperatureThe mixture was cooled to 0° C.
  3. stirringAfter stirring at room temperature for 2 h
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with 1M hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washthe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-f9a788139848407f86e2ee34bc14aa84
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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