4-methylimidazolidine-2-thione

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

Procedure: To a stirred suspension of 4-methylimidazoline-2-thione (45.0 g., 0.387 mole; purified by water recrystallization) in ethanol (200 ml., dried over 4A molecular sieve), methyl iodide (54.9 g., 0.387 mole) was added dropwise. The reaction was stirred at room temperature for 4 hr. during which time the solid dissolved. To this solution 4-chlorobenzylamine (54.8 g., 0.387 mole) was added and the solution was heated at reflux for 16 hrs. This solution was added while hot to a solution of sodium (35.6 g., 1.55 gram atom) in ethanol (900 ml., dried over 4A molecular sieve), and ethyl oximinocyanoacetate (5.50 g., 0.387 mole) was added in portions. The mixture was refluxed for 3 hrs. and concentrated in vacuo. Water (600 ml.) was added to the residue and the solution neutralized with HOAc. The orange precipitate was collected, washed with CH3CN and Et2O to give 95.6 g. (77%) orange solid, m.p. 222° -223° (dec.). was added dropwise during which time the solid dissolved the solution was heated at reflux for 16 hrs was added in portions The mixture was refluxed for 3 hrs and concentrated in vacuo Water (600 ml.) was added to the residue The orange precipitate was collected washed with CH3CN and Et2O to give 95.6 g

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

Procedure: The starting material, 4-methyl-2-imidazolin-2-ylhydrazine hydrochloride, is prepared as follows: 4-methylimidazolidin-2-thione and methyl iodide react in refluxing ethanol to give 4-methyl-2-methylthio-2-imidazoline hydroiodide, which upon treatment with hydrazine in boiling ethanol yields 4-methyl-2-imidazolin-2-ylhydrazine hydroiodide. Subsequent treatment with silver chloride in aqueous or ethanol solution then gives the hydrochloride salt melting at 128°-130° C.

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

Procedure: To a stirred suspension of 4-methylimidazoline-2-thione (45.0 g., 0.387 mole; purified by water recrystallization) in ethanol (200 ml., dried over 4A molecular sieve), methyl iodide (54.9 g., 0.387 mole) was added dropwise. The reaction was stirred at room temperature for 4 hr. during which time the solid dissolved. To this solution 4-chlorobenzylamine (54.8 g., 0.387 mole) was added and the solution was heated at reflux for 16 hrs. This solution was added while hot to a solution of sodium (35.6 g., 1.55 gram atom) in ethanol (900 ml., dried over 4A molecular sieve), and ethyl oximinocyanoacetate (5.50 g., 0.387 mole) was added in portions. The mixture was refluxed for 3 hrs. and concentrated in vacuo. Water (600 ml.) was added to the residue and the solution neutralized with HOAc. The orange precipitate was collected, washed with CH3CN and Et2O to give 95.6 g. (77%) orange solid, m.p. 222° -223° (dec.). was added dropwise during which time the solid dissolved the solution was heated at reflux for 16 hrs was added in portions The mixture was refluxed for 3 hrs and concentrated in vacuo Water (600 ml.) was added to the residue The orange precipitate was collected washed with CH3CN and Et2O to give 95.6 g

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

Procedure: To a stirred suspension of 4-methylimidazoline-2-thione (45.0 g., 0.387 mole; purified by water recrystallization) in ethanol (200 ml., dried over 4A molecular sieve), methyl iodide (54.9 g., 0.387 mole) was added dropwise. The reaction was stirred at room temperature for 4 hr. during which time the solid dissolved. To this solution 4-chlorobenzylamine (54.8 g., 0.387 mole) was added and the solution was heated at reflux for 16 hrs. This solution was added while hot to a solution of sodium (35.6 g., 1.55 gram atom) in ethanol (900 ml., dried over 4A molecular sieve), and ethyl oximinocyanoacetate (5.50 g., 0.387 mole) was added in portions. The mixture was refluxed for 3 hrs. and concentrated in vacuo. Water (600 ml.) was added to the residue and the solution neutralized with HOAc. The orange precipitate was collected, washed with CH3CN and Et2O to give 95.6 g. (77%) orange solid, m.p. 222°-223° (dec.). was added dropwise during which time the solid dissolved the solution was heated at reflux for 16 hrs was added in portions The mixture was refluxed for 3 hrs and concentrated in vacuo Water (600 ml.) was added to the residue The orange precipitate was collected washed with CH3CN and Et2O to give 95.6 g

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

Procedure: The starting material, 4-methyl-2-imidazolin-2-ylhydrazine hydrochloride, is prepared as follows: 4-methylimidazolidin-2-thione and methyl iodide react in refluxing ethanol to give 4-methyl-2-methylthio-2-imidazoline hydroiodide, which upon treatment with hydrazine in boiling ethanol yields 4-methyl-2-imidazolin-2-ylhydrazine hydroiodide. Subsequent treatment with silver chloride in aqueous or ethanol solution then gives the hydrochloride salt melting at 128°-130° C.

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

Procedure: To a stirred suspension of 4-methylimidazoline-2-thione (45.0 g., 0.387 mole; purified by water recrystallization) in ethanol (200 ml., dried over 4A molecular sieve), methyl iodide (54.9 g., 0.387 mole) was added dropwise. The reaction was stirred at room temperature for 4 hr. during which time the solid dissolved. To this solution 4-chlorobenzylamine (54.8 g., 0.387 mole) was added and the solution was heated at reflux for 16 hrs. This solution was added while hot to a solution of sodium (35.6 g., 1.55 gram atom) in ethanol (900 ml., dried over 4A molecular sieve), and ethyl oximinocyanoacetate (5.50 g., 0.387 mole) was added in portions. The mixture was refluxed for 3 hrs. and concentrated in vacuo. Water (600 ml.) was added to the residue and the solution neutralized with HOAc. The orange precipitate was collected, washed with CH3CN and Et2O to give 95.6 g. (77%) orange solid, m.p. 222° -223° (dec.). was added dropwise during which time the solid dissolved the solution was heated at reflux for 16 hrs was added in portions The mixture was refluxed for 3 hrs and concentrated in vacuo Water (600 ml.) was added to the residue The orange precipitate was collected washed with CH3CN and Et2O to give 95.6 g