Triethylamine → Ethyl 2-{4-[2-(2-chlorocinnamoylamino)-ethyl]-phenoxy}-2-methylpropionate

HRID 26795

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=O.C(N(CC)CC)C.ClC(OCC)=O.[NH2:26][CH2:27][CH2:28][C:29]1[CH:43]=[CH:42][C:32]([O:33][C:34]([CH3:41])([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][CH:30]=1>O1CCCC1>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([NH:26][CH2:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:33][C:34]([CH3:40])([CH3:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:42][CH:43]=1)=[O:8]

Participants

Conditions

Temperature: -15 °C

Procedure

To a mixture of 11.50 g. (63 mMol) o-chlorocinnamic acid, 200 ml. anhydrous tetrahydrofuran and 6.38 g. (63 mMol) anhydrous triethylamine, there are added dropwise at -15° C., 7.50 g. (69 mMol) ethyl chloroformate. The reaction mixture is then stirred for 15 minutes at -15° C. Subsequently, a solution of 15.80 g. (63 mMol) ethyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropionate in 50 ml. anhydrous tetrahydrofuran is added dropwise thereto and the reaction mixture is stirred for a further 2 hours at -10° C. and then left to stand for a day at ambient temperature. Thereafter, the tetrahydrofuran is distilled off in a vacuum and the residue is taken up in methylene chloride. The methylene chloride phase is extracted with 0.5 N aqueous sodium hydroxide solution, filtered, dried over anhydrous sodium sulphate and evaporated. After recrystallization of the residue from a mixture of ligroin and acetone (30:5 v/v), there is obtained, in a yield of 65% of theory, ethyl 2-{4-[2-(2-chlorocinnamoylamino)-ethyl]-phenoxy}-2-methylpropionate, which melts at 76° C.

Workup

additionTo a mixture of 11.50 g
stirringthe reaction mixture is stirred for a further 2 hours at -10° C.
waitleft
waitto stand for a day at ambient temperature
distillationThereafter, the tetrahydrofuran is distilled off in a vacuum
extractionThe methylene chloride phase is extracted with 0.5 N aqueous sodium hydroxide solution
filtrationfiltered
dry with materialdried over anhydrous sodium sulphate
customevaporated
customAfter recrystallization of the residue
additionfrom a mixture of ligroin and acetone (30:5 v/v)

Sources & evidence

ORD record: ord-5fefb13f844d4406b6dd0879b3237953
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151303

Linked notes

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