Hydrochloric Acid → HCID 85133399, compound

HRID 2245777Notes

Reaction equation

HRID 2245777 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]([CH3:21])=[CH:8][CH:9]([S:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH3:10])C.[NH2:23][OH:24].[OH-].[K+].CO.Cl>C1COCC1.O>[OH:24][NH:23][C:4](=[O:3])[CH:5]=[CH:6][C:7]([CH3:21])=[CH:8][CH:9]([S:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 887MethanolHCID 14797Potassium HydroxideHCID 73067185HCID 73067185, compound

Product 1

HCID 85133399HCID 85133399, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-(4-dimethylaminophenylsulfanyl)-4-methylhepta-2,4-dienoic acid ethyl ester (0.576 g, 1.80 mmol) in dry THF (10 mL) was added at 0° C. an aqueous solution of hydroxylamine (50%, 1.1 mL, 16.6 mmol). To this mixture was added a solution of potassium hydroxide in methanol (1M, 2.9 mL, 2.9 mmol) over a period of 40 minutes at 0° C. The mixture was stirred at 20° C. for 16 hours, and water (10 mL) was then added. The solution was acidified to pH 5 by addition of concentrated hydrochloric acid (10 M, CAUTION), then extracted with ethyl acetate (50 mL). The organic layer was washed with brine (25 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The yellow oil was dissolved in a mixture of 1:1 diethyl ether:methanol (20 mL) and 20 drops of concentrated hydrochloric (10 M) were added. The crude mixture was evaporated to dryness to give an oil that was triturated with a mixture of diethyl ether and ethanol to give the title compound (0.34 g, 52%) as an off-white solid, mp 177-178° C. (decomp).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with brine (25 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe yellow oil was dissolved in a mixture of 1:1 diethyl ether
  7. additionmethanol (20 mL) and 20 drops of concentrated hydrochloric (10 M) were added
  8. customThe crude mixture was evaporated to dryness
  9. customto give an oil that
  10. customwas triturated with a mixture of diethyl ether and ethanol

Sources & evidence

ORD record
ord-866830e264334e86af9e74a1f9d86378
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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