Triethylamine → methyl 4-[N-[2-(3-cyanophenoxy)ethyl)carbamoyl]benzoate

HRID 747662

Reaction equation

HRID 747662 reaction equation
Br.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].C(N(CC)CC)C.[Cl-].[C:22]([O:33][CH3:34])(=[O:32])[C:23]1[CH:31]=[CH:30][C:26]([C:27]([O-])=[O:28])=[CH:25][CH:24]=1>CN(C)C=O.Cl>[C:9]([C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[O:5][CH2:4][CH2:3][NH:2][C:27]([C:26]1[CH:30]=[CH:31][C:23]([C:22]([O:33][CH3:34])=[O:32])=[CH:24][CH:25]=1)=[O:28])#[N:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 177887733-(2-Aminoethoxy)benzonitrile hydrobromideHCID 22493623Monomethyl terephthalate chloride

Product 1

HCID 68830761methyl 4-[N-[2-(3-cyanophenoxy)ethyl)carbamoyl]benzoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

1.50 g (6.2 mmol) of 3-(2-aminoethoxy)benzonitrile hydrobromide and 3 ml of triethylamine were stirred in 15 ml of dimethylformamide under cooling with ice. 1.23 g (6.2 mmol) of monomethyl terephthalate chloride was slowly added thereto, and they were stirred for 3 hours. The temperature was elevated to the room temperature, and the reaction liquid was diluted with 1 N hydrochloric acid. After the extraction with ethyl acetate, the organic layer was washed with a 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 title compound.

Workup

  1. temperatureunder cooling with ice
  2. customwas elevated to the room temperature
  3. customthe reaction liquid
  4. extractionAfter the extraction with ethyl acetate
  5. washthe organic layer was washed with a 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-5ebf417277be4a51b4f7be0c7c0f2d75
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Linked notes

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