Hydrochloric Acid → 4-[4-(3-cyanophenoxy)butyryl]-N,N-dimethylbenzamide

HRID 747713Notes

Reaction equation

HRID 747713 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)=[O:11])#[N:2].Cl.[CH3:25][N:26](C)[CH2:27]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.CNC.Cl>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([N:26]([CH3:27])[CH3:25])=[O:17])=[CH:14][CH:13]=1)=[O:11])#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68830789HCID 68830789, compound

Product 1

HCID 688360544-[4-(3-cyanophenoxy)butyryl]-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

240 mg (0.78 mmol) of 4-[4-(3-cyanophenoxy)butyryl]benzoic acid, 150 mg (0.78 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 121 mg (0.78 mmol) of 1-hydroxybenzotriazole (hydrous, 87%) and 100 mg of 50% aqueous dimethylamine solution were stirred together in 5 ml of dimethylformamide at room temperature overnight. 1 N hydrochloric acid was added to the resultant mixture. After the extraction with dichloromethane, the extract was washed with saturated aqueous sodium hydrogencarbonate solution and then with saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by the silica gel chromatography with ethyl acetate as the eluent to obtain the title compound.

Workup

  1. extractionAfter the extraction with dichloromethane
  2. washthe extract was washed with saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialwith saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customThe residue was purified by the silica gel chromatography with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-e412be62f8924e6190145c9372ba73cc
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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