2-(dimethylamino)acetohydrazide;hydrochloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N,N-dimethylglycine hydrazide hydrochloride (50 g, 0.263 mol) was stirred for 5 min in EtOH (525 mL). To this suspension was added Cs2CO3 (62.5 g, 0.192 mol) and the mixture was stirred at room temperature for 15 min. Methyl isothiocyanate (19.25 g, 0.263 mol) in EtOH (270 mL) was added to the pot and the reaction mixture was brought to reflux. The reflux condenser was removed and the EtOH was allowed to evaporate under atmospheric pressure (oil bath temperature 105–110° C.) over 3 h to give a purple paste. The reaction was removed from heat and allowed to sit at room temperature overnight (18 h), during which time the paste became a solid. The solid was mixed with CH2Cl2 (1.5 L) and filtered. The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil. The oil was purified by column chromatography through silica gel, eluting with 4:1 CH2Cl2/MeOH to afford 15.3 g (34.9%) of the desired product. to reflux The reflux condenser was removed to evaporate under atmospheric pressure (oil bath temperature 105–110° C.) over 3 h to give a purple paste The reaction was removed from heat to sit at room temperature overnight (18 h) The solid was mixed with CH2Cl2 (1.5 L) filtered The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil The oil was purified by column chromatography through silica gel eluting with 4:1 CH2Cl2/MeOH

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-thione (4 g) was added to a solution of dimethylaminoacetic hydrazide hydrochloride (2 g) and triethylamine (2.4 ml) in dimethylformamide (25 ml). The mixture was refluxed overnight, cooled, and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2.5% methanol/dichloromethane). The appropriate fractions were triturated with dry ether to yield 2.4 g (47.2%) of product, mp 164°-165° C. The mixture was refluxed overnight cooled concentrated under reduced pressure The residue was purified by high performance liquid chromatography (2.5% methanol/dichloromethane) The appropriate fractions were triturated with dry ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2,6-diacetylpyridine (Aldrich Chemical, Milwaukee, Wis., 0.815 g, 5 mmole) in hot ethanol (10 ml) was mixed with a solution of dimethylaminoacethydrazide hydrochloride (Avocado/Alfa Aesar, Ward Hill, Mass.) in warm water (10 ml). The mixture was heated to reflux briefly and allowed to cool. After 3 hrs the mixture was diluted with 20 ml isopropanol, causing a copious precipitate to form. The precipitate was filtered out and washed with isopropanol. Drying gave 2.065 g (95%) white crystalline solid, melting pt. 280-282° C. (dec.). The mixture was heated to reflux briefly to cool to form The precipitate was filtered out washed with isopropanol Drying

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin6-thione (4 g) was added to a solution of dimethylaminoacetic hydrazide hydrochloride (2 g) and triethylamine (2.4 ml) in dimethylformamide (25 ml). The mixture was refluxed overnight, cooled, and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2.5% methano/dichloromethane). The appropriate fractions were triturated with dry ether to yield 2.4 g (47.2%) of product, mp 164°-165° C. The mixture was refluxed overnight cooled concentrated under reduced pressure The residue was purified by high performance liquid chromatography (2.5% methano/dichloromethane) The appropriate fractions were triturated with dry ether

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N,N-dimethylglycine hydrazide hydrochloride (50 g, 0.263 mol) was stirred for 5 min in EtOH (525 mL). To this suspension was added Cs2CO3 (62.5 g, 0.192 mol) and the mixture was stirred at room temperature for 15 min. Methyl isothiocyanate (19.25 g, 0.263 mol) in EtOH (270 mL) was added to the pot and the reaction mixture was brought to reflux. The reflux condenser was removed and the EtOH was allowed to evaporate under atmospheric pressure (oil bath temperature 105-110° C.) over 3H to give a purple paste. The reaction was removed from heat and allowed to sit at room temperature overnight (18H), during which time the paste became a solid. The solid was mixed with CH2Cl2 (1.5 L) and filtered. The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil. The oil was purified by column chromatography through silica gel, eluting with 4:1 CH2Cl2/MeOH to afford 15.3 g (34.9%) of the desired product. 1H NMR (DMSO-d6) d 2.17 (s, 6H) 3.46 (s, 5H) 13.57 (s, 1H). MS (APCI) calcd for C6H12N4S: 172.25; found (M−H+) 171.1. to reflux The reflux condenser was removed to evaporate under atmospheric pressure (oil bath temperature 105-110° C.) over 3H to give a purple paste The reaction was removed from heat to sit at room temperature overnight The solid was mixed with CH2Cl2 (1.5 L) filtered The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil The oil was purified by column chromatography through silica gel eluting with 4:1 CH2Cl2/MeOH

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N,N-dimethylglycine hydrazide hydrochloride (50 g, 0.263 mol) was stirred for 5 min in EtOH (525 mL). To this suspension was added Cs2CO3 (62.5 g, 0.192 mol) and the mixture was stirred at room temperature for 15 min. Methyl isothiocyanate (19.25 g, 0.263 mol) in EtOH (270 mL) was added to the pot and the reaction mixture was brought to reflux. The reflux condenser was removed and the EtOH was allowed to evaporate under atmospheric pressure (oil bath temperature 105–110° C.) over 3 h to give a purple paste. The reaction was removed from heat and allowed to sit at room temperature overnight (18 h), during which time the paste became a solid. The solid was mixed with CH2Cl2 (1.5 L) and filtered. The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil. The oil was purified by column chromatography through silica gel, eluting with 4:1 CH2Cl2/MeOH to afford 15.3 g (34.9%) of the desired product. to reflux The reflux condenser was removed to evaporate under atmospheric pressure (oil bath temperature 105–110° C.) over 3 h to give a purple paste The reaction was removed from heat to sit at room temperature overnight (18 h) The solid was mixed with CH2Cl2 (1.5 L) filtered The organic filtrate was concentrated under reduced pressure to give 31 g of a crude yellow oil The oil was purified by column chromatography through silica gel eluting with 4:1 CH2Cl2/MeOH

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1,2-Dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-thione (4 g) was added to a solution of dimethylaminoacetic hydrazide hydrochloride (2 g) and triethylamine (2.4 ml) in dimethylformamide (25 ml). The mixture was refluxed overnight, cooled, and concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (2.5% methanol/dichloromethane). The appropriate fractions were triturated with dry ether to yield 2.4 g (47.2%) of product, mp 164°-165° C. The mixture was refluxed overnight cooled concentrated under reduced pressure The residue was purified by high performance liquid chromatography (2.5% methanol/dichloromethane) The appropriate fractions were triturated with dry ether