Hydrochloric Acid → HCID 68831194, compound

HRID 747731Notes

Reaction equation

HRID 747731 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)=[O:4].ClC(OCC)=O.Cl.[NH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[I:34])[C:29]#[N:30].Cl>CN(C)C=O.C(N(CC)CC)C>[I:34][C:33]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][C:26]=1[O:25][CH2:24][CH2:23][NH:22][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([C:3](=[O:4])[N:2]([CH3:1])[CH3:14])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 110954804-(Dimethylcarbamoyl)benzoic acidHCID 177889693-(2-Aminoethoxy)-4-iodobenzonitrile monohydrochloride

Product 1

HCID 68831194HCID 68831194, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

600 mg (3.1 mmol) of 4-dimethylcarbamoylbenzoic acid and 1.25 g of triethylamine were stirred in dimethylformamide. 336 mg (3.1 mmol) of ethyl chloroformate was added to the resultant mixture, and they were stirred for 5 minutes. 3-(2-aminoethoxy)-4-iodobenzonitrile monohydrochloride was added to the mixture. The temperature was elevated to room temperature. After stirring for 2 hours, 1 N hydrochloric acid was added to the mixture. After extracting with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl a solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was washed with ethyl acetate to obtain the title compound. Further, the residue obtained after the evaporation of the solvent from the wash solution was purified by the silica gel chromatography (ethyl acetate/methanol) to obtain the title compound.

Workup

  1. customwas elevated to room temperature
  2. stirringAfter stirring for 2 hours
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous NaCl a solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-967026c789834a65b7cc951ef78cf404
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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