Hydrochloric Acid → HCID 90417036, compound

HRID 633596Notes

Reaction equation

HRID 633596 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[C:14]1[C:22]2[C:17](=[C:18]([O:23]C)[N:19]=[CH:20][CH:21]=2)[N:16]([CH3:25])[CH:15]=1.Cl>O1CCOCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[C:14]1[C:22]2[CH:21]=[CH:20][NH:19][C:18](=[O:23])[C:17]=2[N:16]([CH3:25])[CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90417101HCID 90417101, compound

Product 1

HCID 90417036HCID 90417036, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of Example 2C (1.133 g, 2.75 mmol) in dioxane (35 mL) was treated with 4 N HCl in dioxane (35 mL, 140 mmol) and stirred at 70° C. overnight. The solution was cooled, diluted with 200 mL ethyl acetate, then washed with 200 mL of 1:1 saturated aqueous sodium chloride/sodium bicarbonate and dried over anhydrous sodium sulfate. Filtration and solvent removal provided 1.085 g of the product as a yellow solid.

Workup

  1. temperatureThe solution was cooled
  2. washwashed with 200 mL of 1:1 saturated aqueous sodium chloride/sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-ce9b77922ab9493a8caf1a1d9672c555
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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