Ethyl 3-(dimethylamino)-2-(4-hexylphenyl)acrylate → HCID 178442351, compound

HRID 244952Notes

Reaction equation

HRID 244952 reaction equation
CN(C)C=[C:4]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:11]=1)[C:5](OCC)=[O:6].[CH3:23][C:24]([NH:34][NH:35][C:36](OC(C)(C)C)=O)([CH3:33])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1>C(O)(=O)C.C(OCC)C>[CH2:16]([C:13]1[CH:12]=[CH:11][C:10]([C:4]2[CH:36]=[N:35][N:34]([C:24]([CH3:23])([CH3:33])[CH2:25][C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[C:5]=2[OH:6])=[CH:15][CH:14]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 86697470Ethyl 3-(dimethylamino)-2-(4-hexylphenyl)acrylateHCID 86697472Tert-butyl 2-(2-methyl-1-(p-tolyl)propan-2-yl)hydrazinecarboxylate

Product 1

HCID 178442351HCID 178442351, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 3-(dimethylamino)-2-(4-hexylphenyl)acrylate and 0.50 g (1.8 mmol) of tert-butyl 2-(2-methyl-1-(p-tolyl)propan-2-yl)hydrazinecarboxylate were dissolved in 2 mL of acetic acid and stirred at 90° C. for 24 hours. After the stirring, the reaction mixture was mixed with 0.5 mL of acetic acid and stirred for 48 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with diethyl ether and washed with distilled water, with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel 30 g, ethyl acetate:hexane=0:100 to 35:65). The resulting solid was washed with isopropyl ether to give 164 mg of the desired product as a white solid.

Workup

  1. stirringstirred for 48 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. washwashed with distilled water, with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel 30 g, ethyl acetate:hexane=0:100 to 35:65)
  9. washThe resulting solid was washed with isopropyl ether

Sources & evidence

ORD record
ord-7894eb2ebe044972a9dd513290bbc7e4
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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