1,3-thiazolidine;hydrochloride

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50°C for 2 hours. The precipitate was filtered at 5° - 10°C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120°C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200°C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N, 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50°C for 2 hours The precipitate was filtered at 5° - 10°C washed by vacuum-drying at 120°C to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50°C for 2 hours. The precipitate was filtered at 5° - 10°C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120°C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200°C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N, 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50°C for 2 hours The precipitate was filtered at 5° - 10°C washed by vacuum-drying at 120°C to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50° C for 2 hours. The precipitate was filtered at 5° - 10° C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120° C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200° C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N. 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50° C for 2 hours The precipitate was filtered at 5° - 10° C washed by vacuum-drying at 120° C to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50°C for 2 hours. The precipitate was filtered at 5° - 10°C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120°C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200°C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N, 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50°C for 2 hours The precipitate was filtered at 5° - 10°C washed by vacuum-drying at 120°C to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50°C for 2 hours. The precipitate was filtered at 5° - 10°C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120°C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200°C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N, 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50°C for 2 hours The precipitate was filtered at 5° - 10°C washed by vacuum-drying at 120°C to give 147.8 g

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

Procedure: A mixture containing 10.51 g (0.05 mol) of 1,3-diphenylpropan-1-one, 6.28 g (0.05 mol) of thiazolidine hydrochloride, 3.75 g (0.125 mol) of paraformaldehyde and 25 ml of 37% hydrochloric acid is stirred under reflux for 6 hours. After cooling down, 2.50 g of a white product precipitate from the reaction mixture which is unchanged thiazolidine hydrochloride. After evaporating the filtrate, the light yellow residue weighing 16.52 g is washed thoroughly 3 times with 20 ml of ether each. Thus, 7.80 g of a white powder-like substance are obtained which is suspended in water and the insoluble part is twice recrystallized from 2-propanol to obtain 3.50 g (20.1%) of hydrochloride of the title compound, m.p.: 134° C. under reflux for 6 hours After cooling down After evaporating the filtrate is washed thoroughly 3 times with 20 ml of ether each

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

Procedure: A mixture containing 10.51 g (0.05 mol) of 1,3-diphenylpropan-1-one, 6.28 g (0.05 mol) of thiazolidine hydrochloride, 3.75 g (0.125 mol) of paraformaldehyde and 25 ml of 37% hydrochloric acid is stirred under reflux for 6 hours. After cooling down, 2.50 g of a white product precipitate from the reaction mixture which is unchanged thiazolidine hydrochloride. After evaporating the filtrate, the light yellow residue weighing 16.52 g is washed thoroughly 3 times with 20 ml of ether each. Thus, 7.80 g of a white powder-like substance are obtained which is suspended in water and the insoluble part is twice recrystallized from 2-propanol to obtain 3.50 g (20.1%) of hydrochloride of the title compound, m.p.: 134° C. under reflux for 6 hours After cooling down After evaporating the filtrate is washed thoroughly 3 times with 20 ml of ether each

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50° C for 2 hours. The precipitate was filtered at 5° - 10° C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120° C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200° C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50° C for 2 hours The precipitate was filtered at 5° - 10° C washed by vacuum-drying at 120° C to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50°C for 2 hours. The precipitate was filtered at 5° - 10°C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120°C. to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200°C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50°C for 2 hours The precipitate was filtered at 5° - 10°C washed by vacuum-drying at 120°C. to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50° C for 2 hours. The precipitate was filtered at 5° - 10° C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120° C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200° C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N. 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50° C for 2 hours The precipitate was filtered at 5° - 10° C washed by vacuum-drying at 120° C to give 147.8 g

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

Procedure: While cooling and stirring 250 g. of pyridine, 175 g. (1.40 moles) of thiazolidine hydrochloride [preparation described by S. Ratner and H. Clarke, J. Am. Chem. Soc. 59, 200 (1937)] was added. After it had dissolved, 106.4 g. (1.40 mole) of carbon disulfide was added dropwise, followed by 128.5 g. (0.70 mole) of anhydrous zinc acetate. The resulting reaction mixture was stirred at 40° - 50°C for 2 hours. The precipitate was filtered at 5° - 10°C. The crude solid was water-washed and finally freed of pyridine by vacuum-drying at 120°C to give 147.8 g. of the desired product. It gradually decomposed starting at ca. 200°C without a definite final decomposition point. A small sample washed with hot benzene had the following analysis: Found: C, 24.46; H, 2.95; N, 7.31; Zn, 16.58%. Calcd for C8H12N2S6Zn: C, 24.40; H, 3.05; N, 7.12; Zn, 16.62%. While cooling After it had dissolved The resulting reaction mixture was stirred at 40° - 50°C for 2 hours The precipitate was filtered at 5° - 10°C washed by vacuum-drying at 120°C to give 147.8 g