Hydrochloric Acid → HCID 17788774, compound

HRID 747716Notes

Reaction equation

HRID 747716 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)#[N:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1.Cl>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([NH:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1)=[O:12])#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 133964-AminobenzonitrileHCID 17788959HCID 17788959, compound

Product 1

HCID 17788774HCID 17788774, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.49 mmol) of 4-(3-cyanophenoxy)butyric acid and 50 mg (0.49 mmol) of triethylamine were stirred in dimethylformamide under cooling with ice. 53 mg (0.49 mmol) of ethyl chloroformate was added to the resultant mixture. After stirring for 2 minutes, 58 mg (0.49 mmol) of p-aminobenzonitrile was added to the reaction mixture. The temperature was elevated to room temperature, and they were stirred overnight. 1 N hydrochloric acid was added to the reaction mixture. After the extraction with ethyl acetate, the extract was washed with saturated aqueous sodium hydrogencarbonate solution and then with saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated to obtain the crude title compound.

Workup

  1. temperatureunder cooling with ice
  2. customwas elevated to room temperature
  3. stirringthey were stirred overnight
  4. extractionAfter the extraction with ethyl acetate
  5. washthe extract was washed with saturated aqueous sodium hydrogencarbonate solution
  6. dry with materialwith saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4e9c95c0c13d466f883d35a2521e0382
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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