Water → HCID 68085473, compound

HRID 1423965Notes

Reaction equation

S(Cl)(Cl)=O.C(N([CH:11]([CH3:13])[CH3:12])C(C)C)C.[CH:14]1([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[OH2:27].[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH:14]1([N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:31](=[O:27])/[CH:30]=[CH:29]/[C:28]2[CH:34]=[C:11]([CH3:12])[CH:13]=[CH:32][CH:33]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

Reactant 5

HCID 962Water

HCID 1140Toluene3×

HCID 24386Thionyl Chloride2×

HCID 81531Diisopropylethylamine

HCID 84957N-Cyclohexylpyridin-2-amine

Product 1

HCID 68085473HCID 68085473, compoundYield 74%

Conditions

Temperature: 60 °C

Procedure

4.87 g (0.03 mol) of 3-methylcinammic acid, 49 ml of toluene and 0.19 g (2.6 mmol) of N,N-dimethylormamide are provided and mixed with 4.3 g (0.036 mol) of thionyl chloride. Stirring takes place for 1 hour followed by heating to 60° C. The toluene and excess thionyl chloride are drawn off under vacuum. Then 24 ml of toluene and 4.3 g (0.033 mol) of ethyldiisopropylamine are added at 60° C. A solution of 5.8 g (0.033 mol) of cyclohexyl-2-pyridinylamine (for preparation see E. H. Mørkved, Journal f. prakt.Chemie, 1986, 328 (3), 401-406) in toluene is added and stirred for 2 hours at 60-65° C. Hydrolysis with water is performed and the organic phase is washed with water, 1 N NaOH and again with water. The organic phase is rotated and the residue crystallised from MTBE. The crystallised solid is drawn off, washed with MTBE and dried, wherein the desired compound is obtained.

Workup

customfor 1 hour
stirringstirred for 2 hours at 60-65° C
washthe organic phase is washed with water, 1 N NaOH and again with water
customthe residue crystallised from MTBE
washwashed with MTBE
customdried

Sources & evidence

ORD record: ord-1cfa6206fe454ea0b426957bd1cec50f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927605B2

Reaction notes

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