1-[(2-fluorobenzoyl)amino]-3-methylthiourea

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 1-(2-Fluorobenzoyl)-4-methylthiosemicarbazide (11.3 g, 4.97×10-2 mole) or the aforementioned mixture of the above and pyridine hydrochloride and 1 molar aqueous NaHCO3 (480 ml, 4.80×10-1 mole) were stirred and heated to reflux. After refluxing overnight, the reaction was cooled in an ice bath before being acidified by the dropwise addition of concentrated hydrochloric acid (40 ml, 4.8×10-1 mole). The resulting precipitate was collected by filtration, washed with a little H2O, and dried by suction. This afforded a colorless powder. This material was of sufficient purity to go on to the next step. If desired this material could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C. heated to reflux After refluxing overnight the reaction was cooled in an ice bath The resulting precipitate was collected by filtration washed with a little H2O dried by suction This afforded a colorless powder could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C.

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

実験手順: 1-(2-Fluorobenzoyl)-4-methylthiosemicarbazide (11.3 g, 4.97×10-2 mole) or the aforementioned mixture of the above and pyridine hydrochloride and 1 molar aqueous NaHCO3 (480 ml, 4.80×10-1 mole) were stirred and heated to reflux. After refluxing overnight, the reaction was cooled in an ice bath before being acidified by the dropwise addition of concentrated hydrochloric acid (40 ml, 4.8×10-1 mole). The resulting precipitate was collected by filtration, washed with a little H2O, and dried by suction. This afforded a colorless powder. This material was of sufficient purity to go on to the next step. If desired this material could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C. heated to reflux After refluxing overnight the reaction was cooled in an ice bath The resulting precipitate was collected by filtration washed with a little H2O dried by suction This afforded a colorless powder could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C.

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

実験手順: To a stirred room temperature suspension of 4-methylthiosemicarbazide (7.9 g, 7.5×10-2 mole) and CHCl3 (190 ml), 2-fluorobenzoyl chloride (9.4 ml, 7.9×10-2 mole) was added dropwise. After stirring overnight at room temperature, the precipitate was collected by filtration and the product was washed with two portions of Et2O. Drying by suction gave a colorless powder which was used without further purification in the subsequent cyclization step. was added dropwise the precipitate was collected by filtration the product was washed with two portions of Et2O Drying by suction gave a colorless powder which was used without further purification in the subsequent cyclization step

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

実験手順: To a stirred room temperature suspension of 4-methylthiosemicarbazide (7.9 g, 7.5×10-2 mole) and CHCl3 (190 ml), 2-fluorobenzoyl chloride (9.4 ml, 7.9×10-2 mole) was added dropwise. After stirring overnight at room temperature, the precipitate was collected by filtration and the product was washed with two portions of Et2O. Drying by suction gave a colorless powder which was used without further purification in the subsequent cyclization step. was added dropwise the precipitate was collected by filtration the product was washed with two portions of Et2O Drying by suction gave a colorless powder which was used without further purification in the subsequent cyclization step

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

実験手順: 1-(2-Fluorobenzoyl)-4-methylthiosemicarbazide (11.3 g, 4.97×10-2 mole) or the aforementioned mixture of the above and pyridine hydrochloride and 1 molar aqueous NaHCO3 (480 ml, 4.80×10-1 mole) were stirred and heated to reflux After refluxing overnight, the reaction was cooled in an ice bath before being acidified by the drop-wise addition of concentrated hydrochloric acid (40 ml, 4.8×10-1 mole). The resulting precipitate was collected by filtration, washed with a little H2O, and dried by suction. This afforded a colorless powder 5.0 g (48%). This material was of sufficient purity to go on to the next step. If desired this material could be crystallized from EtOAc/hexane affording colorless needles, mp 137°-139° C. heated to reflux After refluxing overnight the reaction was cooled in an ice bath The resulting precipitate was collected by filtration washed with a little H2O dried by suction

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

実験手順: To a stirred room temperature solution of 4-methylthiosemicarbazide (10.5 g, 1.00×10-1 mole) and pyridine (250 ml), 2-fluorobenzoyl chloride (11.9 ml, 1.00×10-1 mole) was added dropwise. After stirring overnight at room temperature the excess pyridine was evaporated at reduced pressure first on a rotary evaporator and then at high vacuum. This afforded a mixture of the desired product and pyridine hydrochloride which is used without further purification in the subsequent cyclization step. was evaporated at reduced pressure first on a rotary evaporator This afforded

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

実験手順: To a stirred room temperature solution of 4-methylthiosemicarbazide (10.5 g, 1.00×10-1 mole) and pyridine (250 ml), 2-fluorobenzoyl chloride (11.9 ml, 1.00×10-1 mole) was added dropwise. After stirring overnight at room temperature the excess pyridine was evaporated at reduced pressure first on a rotary evaporator and then at high vacuum. This afforded a mixture of the desired product and pyridine hydrochloride which is used without further purification in the subsequent cyclization step. was evaporated at reduced pressure first on a rotary evaporator This afforded

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

実験手順: 1-(2-Fluorobenzoyl)-4-methylthiosemicarbazide (11.3 g, 4.97×10-2 mole) or the aforementioned mixture of the above and pyridine hydrochloride and 1 molar aqueous NaHCO3 (480 ml, 4.80×10-1 mole) were stirred and heated to reflux. After refluxing overnight, the reaction was cooled in an ice bath before being acidified by the dropwise addition of concentrated hydrochloric acid (40 ml, 4.8×10-1 mole). The resulting precipitate was collected by filtration, washed with a little H2O, and dried by suction. This afforded a colorless powder. This material was of sufficient purity to go on to the next step. If desired this material could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C. heated to reflux After refluxing overnight the reaction was cooled in an ice bath The resulting precipitate was collected by filtration washed with a little H2O dried by suction This afforded a colorless powder could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C.

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

実験手順: 1-(2-Fluorobenzoyl)-4-methylthiosemicarbazide (11.3 g, 4.97×10-2 mole) or the aforementioned mixture of the above and pyridine hydrochloride and 1 molar aqueous NaHCO3 (480 ml, 4.80×10-1 mole) were stirred and heated to reflux. After refluxing overnight, the reaction was cooled in an ice bath before being acidified by the dropwise addition of concentrated hydrochloric acid (40 ml, 4.8×10-1 mole). The resulting precipitate was collected by filtration, washed with a little H2O, and dried by suction. This afforded a colorless powder. This material was of sufficient purity to go on to the next step. If desired this material could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C. heated to reflux After refluxing overnight the reaction was cooled in an ice bath The resulting precipitate was collected by filtration washed with a little H2O dried by suction This afforded a colorless powder could be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C.

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

実験手順: To a stirred room temperature solution of 4-methylthiosemicarbazide (10.5 g, 1.00×10-1 mole) and pyridine (250 ml), 2-fluorobenzoyl chloride (11.9 ml, 1.00×10-1 mole) was added dropwise. After stirring overnight at room temperature the excess pyridine was evaporated at reduced pressure first on a rotary evaporator and then at high vacuum. This afforded a mixture of the desired product and pyridine hydrochloride which is used without further purification in the subsequent cyclization step. was evaporated at reduced pressure first on a rotary evaporator This afforded

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

実験手順: To a stirred room temperature solution of 4-methylthiosemicarbazide (10.5 g, 1.00×10-1 mole) and pyridine (250 ml), 2-fluorobenzoyl chloride (11.9 ml, 1.00×10-1 mole) was added dropwise. After stirring overnight at room temperature the excess pyridine was evaporated at reduced pressure first on a rotary evaporator and then at high vacuum. This afforded a mixture of the desired product and pyridine hydrochloride which is used without further purification in the subsequent cyclization step. was evaporated at reduced pressure first on a rotary evaporator This afforded