N-carbamothioyl-2-methylpropanamide

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

実験手順: 11A (29.6 g, 0.2 mol) was dissolved in anhydrous EtOH (300 mL). To the solution was added 3-bromo-2-oxo-propionic acid (34 g, 0.17 mol). The mixture was refluxed for 2 hours, then cooled to room temperature, concentrated to dryness, dissolved with ethyl acetate, washed with saturated aqueous of NaHCO3. The organic layer was dried and concentrated to give a crude product 11B (48 g, 100% yield). The mixture was refluxed for 2 hours concentrated to dryness dissolved with ethyl acetate washed with saturated aqueous of NaHCO3 The organic layer was dried concentrated

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

実験手順: 11A (29.6 g, 0.2 mol) was dissolved in anhydrous EtOH (300 mL). To the solution was added 3-bromo-2-oxo-propionic acid (34 g, 0.17 mol). The mixture was refluxed for 2 hours, then cooled to room temperature, concentrated to dryness, dissolved with ethyl acetate, washed with saturated aqueous of NaHCO3. The organic layer was dried and concentrated to give a crude product 11B (48 g, 100% yield). The mixture was refluxed for 2 hours concentrated to dryness dissolved with ethyl acetate washed with saturated aqueous of NaHCO3 The organic layer was dried concentrated

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

実験手順: Thiourea (152 g, 2 mol) was dissolved in toluene (1520 mL). To the solution was added isobutyryl chloride (213 g, 2 mol) under mechanical stirring. The reaction mixture was refluxed for 3 hours. TLC monitored the reaction. After the reaction completed, the reaction mixture was cooled to room temperature and filtered to remove insoluble solids. The filtrate was concentrated to dryness. The yellow solids were collected by filtration, washed with petroleum ether (100 mL×3) to appear white, dried in vacumm to give the desired product 11A (90 g, 30% yield) as a white solid (mp: 114˜116° C.). The reaction mixture was refluxed for 3 hours the reaction filtered to remove insoluble solids The filtrate was concentrated to dryness The yellow solids were collected by filtration washed with petroleum ether (100 mL×3) dried in vacumm

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

実験手順: A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with water-toluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂ 1.1-1.3 (2×CH3), 1.4- 1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic). A 300 ml reaction flask fitted with a magnetic stirrer heating mantle prepared prepared refluxed for three hours The solvent was removed under reduced pressure the residual solid was stirred with water-toluene

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

実験手順: A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with water-toluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂ 1.1-1.3 (2×CH3), 1.4- 1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic). A 300 ml reaction flask fitted with a magnetic stirrer heating mantle prepared prepared refluxed for three hours The solvent was removed under reduced pressure the residual solid was stirred with water-toluene

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

実験手順: A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with watertoluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂1.1-1.3 (2×CH3), 1.4-1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic). A 300 ml reaction flask fitted with a magnetic stirrer heating mantle prepared prepared refluxed for three hours The solvent was removed under reduced pressure the residual solid was stirred with watertoluene

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

実験手順: 11A (29.6 g, 0.2 mol) was dissolved in anhydrous EtOH (300 mL). To the solution was added 3-bromo-2-oxo-propionic acid (34 g, 0.17 mol). The mixture was refluxed for 2 hours, then cooled to room temperature, concentrated to dryness, dissolved with ethyl acetate, washed with saturated aqueous of NaHCO3. The organic layer was dried and concentrated to give a crude product 11B (48 g, 100% yield). The mixture was refluxed for 2 hours concentrated to dryness dissolved with ethyl acetate washed with saturated aqueous of NaHCO3 The organic layer was dried concentrated

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

実験手順: Thiourea (152 g, 2 mol) was dissolved in toluene (1520 mL). To the solution was added isobutyryl chloride (213 g, 2 mol) under mechanical stirring. The reaction mixture was refluxed for 3 hours. TLC monitored the reaction. After the reaction completed, the reaction mixture was cooled to room temperature and filtered to remove insoluble solids. The filtrate was concentrated to dryness. The yellow solids were collected by filtration, washed with petroleum ether (100 mL×3) to appear white, dried in vacumm to give the desired product 11A (90 g, 30% yield) as a white solid (mp: 114˜116° C.). The reaction mixture was refluxed for 3 hours the reaction filtered to remove insoluble solids The filtrate was concentrated to dryness The yellow solids were collected by filtration washed with petroleum ether (100 mL×3) dried in vacumm

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

実験手順: A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with water-toluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂ 1.1-1.3 (2×CH3), 1.4- 1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic). A 300 ml reaction flask fitted with a magnetic stirrer heating mantle prepared prepared refluxed for three hours The solvent was removed under reduced pressure the residual solid was stirred with water-toluene