Ethyl 2-(2,6-dichlorophenoxy)propanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46.0 g (0.1748 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 212.0 g (3.527 mols) of 1,2-diaminoethane and, after working up, produce 38.0 g (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =-5.8° (c=1/ethanol)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46.0 g (0.1748 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 212.0 g (3.527 mols) of 1,2-diaminoethane and, after working up, produce 38.0 g (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =-5.8° (c=1/ethanol)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a variation of the present process, the (-)-2-(2,6-dichlorophenoxy)-propionic acid ethylester obtained as above described, is reacted with an ethanolic solution of ammonia at room temperature and is converted into (+)-2-(2,6-dichlorophenoxy)-propionic acid amide which is difficultly soluble in ethanol. This amide is dehydrated at from 0° to 30° C. with a titanium tetrachloride/tetrahydrofurane complex and 4-methyl-morpholine in chloroform into (-)-2-(2,6-dichlorophenoxy)-propionic acid nitrile. By introducing hydrogen chloride at 0° C., the nitrile is then converted with ethanol in chloroform into (-)-2-(2,6-dichlorophenoxy)-propionimido acid ethylester hydrochloride. This compound is dissolved in ethanol and is cyclized by adding 1,2-diaminoethane to produce (-)-2-[1-(2,6-dichlorophenoxy)-ethyl]-1,3-diazacyclopent-2-ene. Analogously to the previous process, (-)-2-[1-(2,6-dichlorophenoxy)-ethyl]-1,3-diazacyclopent-2-ene hydrochloride is produced from the (-)-base thus obtained.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: