Hydrochloric Acid → HCID 68762772, compound

HRID 2114158Notes

Reaction equation

HRID 2114158 reaction equation
[C:1]1([CH:7]([C:11](Cl)=[O:12])[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N)C.[O:17]1CCCC1.[CH2:22]([N:24](CC)[CH2:25][CH3:26])[CH3:23].Cl>C(OCC)(=O)C.C(Cl)Cl>[CH2:22]([N:24]([CH2:25][CH3:26])[C:8](=[O:9])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11]([OH:12])=[O:17])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12294915Propanedioyl dichloride, phenyl-HCID 66726184Ethylamine tetrahydrofuran

Product 1

HCID 68762772HCID 68762772, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The phenylmalonic acid dichloride (8.99 g) obtained in Reference Example 1a) was added dropwise to a mixture of ethylamine/tetrahydrofuran (2M, 45.5 mL), triethylamine (13.9 mL) and methylene chloride (80 mL) at −20° C. The reaction temperature was elevated to room temperature, and the mixture was stirred overnight. After addition of 3N hydrochloric acid, the reaction solution was diluted with ethyl acetate, and the organic phase was washed successively with saturated brine, saturated aqueous sodium bicarbonate solution, and saturated brine, dried over sodium sulfate, and then concentrated to give a solid. The solid was washed with ethyl acetate-hexane to give the title compound (4.85 g) as a white powder.

Workup

  1. customwas elevated to room temperature
  2. washthe organic phase was washed successively with saturated brine, saturated aqueous sodium bicarbonate solution, and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a solid
  6. washThe solid was washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-324c11b4403849e18201b9e662f78f6e
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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