Thionyl Chloride → HCID 19088077, compound

HRID 1464502Notes

Reaction equation

HRID 1464502 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1.S(Cl)(Cl)=O.Cl.[NH2:40][OH:41].C(=O)([O-])O.[Na+]>ClCCl.O.CN(C)C=O>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:40][OH:41])=[O:25])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 19088057HCID 19088057, compound

Product 1

HCID 19088077HCID 19088077, compoundYield 120.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 0.92 g (2.0 mmole) of 4-[7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptoxy]benzoic acid in dichloromethane (10 ml) were added 0.44 ml (2×3 mmole) of thionyl chloride and dimethylformamide (8 μl), and the mixture was stirred at 40° C. for 1 hour. The solvent was distilled off, and the residue was dissolved in tetrahydrofuran (10 ml), followed by ice-cooling. After 0.21 g (2×1.5 mmole) of hydroxylamine hydrochloride was added, a solution of 0.34 g (2×2 mmole) of sodium hydrogencarbonate in water (5 ml) was added to the reaction mixture, followed by stirring for 15 minutes under ice-cooling. The tetrahydrofuran was distilled off under reduced pressure, and ethyl acetate was added to the residue to conduct extraction. The ethyl acetate layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residue was chromatographed on a silica gel column to elute with ethyl acetate to give 4-[7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptoxy]benzohydroxamic acid (0.86 g, 91%).

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in tetrahydrofuran (10 ml)
  3. temperaturecooling
  4. stirringby stirring for 15 minutes under ice-
  5. temperaturecooling
  6. distillationThe tetrahydrofuran was distilled off under reduced pressure, and ethyl acetate
  7. additionwas added to the residue
  8. extractionextraction
  9. customThe ethyl acetate layer was separated out
  10. washwashed with aqueous sodium chloride solution
  11. dry with materialdried (magnesium sulfate)
  12. customevaporated
  13. customThe residue was chromatographed on a silica gel column
  14. washto elute with ethyl acetate

Sources & evidence

ORD record
ord-9ed34f5aa9fc43e3b053774b01e4af88
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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