Toluene → N-cyclohexyl-N,3-diphenyl-prop-2-enamide

HRID 1423968Notes

Reaction equation

S(Cl)(Cl)=O.C(N(C(C)C)C(C)C)C.[CH:14]1([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH3:27][CH:28]1[CH2:32][CH2:31][CH2:30][O:29]1.[C:33]1(C)[CH:38]=CC=[CH:35][CH:34]=1>O>[CH:21]1([N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:30](=[O:29])/[CH:31]=[CH:32]/[C:28]2[CH:35]=[CH:34][CH:33]=[CH:38][CH:27]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 50 °C

Procedure

7.60 g (0.051 mol) of cinammic acid, 92 ml of toluene and 0.41 g (5.6 mmol) g of N,N-dimethylormamide are provided and mixed with 7.3 g (0.062 mol) of thionyl chloride. Stirring takes place for 1 hour followed by heating to 50° C. The toluene and excess thionyl chloride are drawn off under vacuum. Then 22 ml of toluene and 7.3 g (0.056 mol) of ethyldiisopropylamine are added at 60° C. A solution of 9.1 g (0.056 mol) of N-cyclohexylaniline in toluene is added and stirred for 1 hour at 60° C. Hydrolysis with water at 50° C. is performed and 2-methyltetrahydrofuran is added. The organic phase is separated and washed with water, 1N hydrochloric acid, 1N NaOH and again with water. The organic phase is rotated and the residue crystallised from n-heptane/MTBE. The crystallised solid is drawn off, washed with n-heptane and dried, wherein the desired compound is obtained.

Workup

customfor 1 hour
stirringstirred for 1 hour at 60° C
customThe organic phase is separated
washwashed with water, 1N hydrochloric acid, 1N NaOH and again with water
customthe residue crystallised from n-heptane/MTBE
washwashed with n-heptane
customdried

Sources & evidence

ORD record: ord-35126c012c914ba9a859847eadfe8dff
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927605B2

Reaction notes

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