57676-49-0

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

Procedure: A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid). the reaction was heated to reflux for 6 hours left to cool The reaction mixture was evaporated to dryness under reduced pressure the solid residue dissolved in water resulting in formation of a white precipitate The precipitate was isolated by filtration washed with water and ether and air dried

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

Procedure: A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid). the reaction was heated to reflux for 6 hours left to cool The reaction mixture was evaporated to dryness under reduced pressure the solid residue dissolved in water resulting in formation of a white precipitate The precipitate was isolated by filtration washed with water and ether and air dried

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

Procedure: Hydrazine hydrate (4.7 cm3) was added dropwise to ethyl (4-methoxyphenyl)acetate (3.73 g) and then methanol (20 cm3) was added to form a homogeneous reaction mixture. This mixture was stirred for 18 hours at ambient temperature during which time a white precipitate formed. The precipitate was isolated by filtration and washed with methanol and water, then air-dried to give (4-methoxyphenyl)acetic acid hydrazide (2 g). M+ =180; 1H NMR: δ 3.50(2H,s); 3.80(3H,s); 3.85(2H,br s); 6.70(1H,br s); 6.90(2H,d); 7.20(2H,d); (solid). to form a homogeneous reaction mixture formed The precipitate was isolated by filtration washed with methanol and water air-dried

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

Procedure: A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid). the reaction was heated to reflux for 6 hours left to cool The reaction mixture was evaporated to dryness under reduced pressure the solid residue dissolved in water resulting in formation of a white precipitate The precipitate was isolated by filtration washed with water and ether and air dried

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

Procedure: A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid). the reaction was heated to reflux for 6 hours left to cool The reaction mixture was evaporated to dryness under reduced pressure the solid residue dissolved in water resulting in formation of a white precipitate The precipitate was isolated by filtration washed with water and ether and air dried

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

Procedure: Hydrazine hydrate (4.7 cm3) was added dropwise to ethyl (4-methoxyphenyl)acetate (3.73 g) and then methanol (20 cm3) was added to form a homogeneous reaction mixture. This mixture was stirred for 18 hours at ambient temperature during which time a white precipitate formed. The precipitate was isolated by filtration and washed with methanol and water, then air-dried to give (4-methoxyphenyl)acetic acid hydrazide (2g). M+ =180; 1H NMR: δ 3.50(2H,s); 380(3H,s); 3.85(2H,br s); 6.70(1H,br s); 6.90(2H,d); 7.20(2H,d); (solid). to form a homogeneous reaction mixture formed The precipitate was isolated by filtration washed with methanol and water air-dried

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

Procedure: The title compound was prepared as described in Example 17 from 4-methoxy-phenylacetic acid hydrazide (1.39 mmol) and 3-chloro-6-thiophen-2-yl-pyridazine (0.32 mmol) as a pale orange solid. 1H NMR (CD3OD) δ 8.17 (1H, d, J=9.8 Hz), 7.92 (1H, dd, J=3.8 Hz, 1.2 Hz), 7.88 (1H, d, J=9.9 Hz), 7.74 (1H, dd, J=5.0 Hz, 1.0 Hz), 7.40 (2H, d, J=8.8 Hz), 7.23 (1H, dd, J=5.0 Hz, 3.8 Hz), 6.88 (2H, d, J=8.9 Hz,), 4.51 (s, 2H), 3.75 (3H, s). ESI-MS (m/z): Calcd for C17H14N4OS: 322.1; found 323.2 (M+H).

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

Procedure: The title compound was prepared as described in Example 17 from 4-methoxy-phenylacetic acid hydrazide (1.39 mmol) and 3-chloro-6-thiophen-2-yl-pyridazine (0.32 mmol) as a pale orange solid. 1H NMR (CD3OD) δ 8.17 (1H, d, J=9.8 Hz), 7.92 (1H, dd, J=3.8 Hz, 1.2 Hz), 7.88 (1H, d, J =9.9 Hz), 7.74 (1H, dd, J=5.0 Hz, 1.0 Hz), 7.40 (2H, d, J=8.8 Hz), 7.23 (1H, dd, J =5.0 Hz, 3.8 Hz), 6.88 (2H, d, J=8.9 Hz,), 4.51 (s, 2H), 3.75 (3H, s). ESI-MS (m/z): Calcd for C17H14N4OS: 322.1; found 323.2 (M+H).

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

Procedure: A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration; washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid). the reaction was heated to reflux for 6 hours left to cool The reaction mixture was evaporated to dryness under reduced pressure the solid residue dissolved in water resulting in formation of a white precipitate The precipitate was isolated by filtration washed with water and ether and air dried

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

Procedure: Hydrazine hydrate (4.7 cm3) was added dropwise to ethyl (4-methoxyphenyl)acetate (3.73 g) and then methanol (20 cm3) was added to form a homogeneous reaction mixture. This mixture was stirred for 18 hours at ambient temperature during which time a white precipitate formed. The precipitate was isolated by filtration and washed with methanol and water, then air-dried to give (4-methoxyphenyl)acetic acid hydrazide (2 g). M+ =180; 1H NMR: δ 3.50(2H,s); 3.80(3H,s); 3.85(2H,br s); 6.70(1H,br s); 6.90(2H,d); 7.20(2H,d); (solid). to form a homogeneous reaction mixture formed The precipitate was isolated by filtration washed with methanol and water air-dried

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

Procedure: A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid). the reaction was heated to reflux for 6 hours left to cool The reaction mixture was evaporated to dryness under reduced pressure the solid residue dissolved in water resulting in formation of a white precipitate The precipitate was isolated by filtration washed with water and ether and air dried

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

Procedure: Hydrazine hydrate (4.7 cm3) was added dropwise to ethyl (4-methoxyphenyl)acetate (3.73 g) and then methanol (20 cm3) was added to form a homogeneous reaction mixture. This mixture was stirred for 18 hours at ambient temperature during which time a white precipitate formed. The precipitate was isolated by filtration and washed with methanol and water, then air-dried to give (4-methoxyphenyl)acetic acid hydrazide (2 g). M+ =180; 1H NMR: δ 3.50(2H,s); 3.80(3H,s); 3.85(2H,br s); 6.70(1H,br s); 6.90(2H,d); 7.20(2H,d); (solid). to form a homogeneous reaction mixture formed The precipitate was isolated by filtration washed with methanol and water air-dried