Methanesulfonyl chloride → HCID 76710727, compound

HRID 1188949Notes

Reaction equation

HRID 1188949 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][CH: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:10]=[CH: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])(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 76710731HCID 76710731, compound

Product 1

HCID 76710727HCID 76710727, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
4 °C

Procedure

To an ice-cooled and stirred solution of ethyl 2-({2-hydroxy-4-[4-(methylsulfonyl)phenoxy]phenyl}hydrazono)propanoate (5.8 g) in pyridine (60 mL) was added methanesulfonyl chloride (1.4 mL), and the mixture was stirred at 4° C. for 1 h and then at room temperature for 3 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 residue was purified by short silica gel chromatography (ethyl acetate) to give light orange crystals, which were washed with ethyl acetate-hexane to give the title compound (6.49 g, 93%) as light orange crystals. MS 471 (MH+).

Workup

  1. waitat room temperature for 3 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and aqueous citric acid solution
  4. washThe organic layer was washed successively with aqueous citric acid solution and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by short silica gel chromatography (ethyl acetate)
  9. customto give light orange crystals, which
  10. washwere washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-e55f5506da3c4ea09efc42ca6d2abca0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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