Tetrahydrofuran → 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224201Notes

Reaction equation

HRID 2224201 reaction equation
C1C[O:4][CH2:3]C1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:30]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)=[CH:29][N:28]=[N:27][C:26]=2[NH:38][NH2:39])=[CH:21][CH:20]=1>O>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([C:30]2[CH:29]=[N:28][N:27]3[C:3](=[O:4])[NH:39][N:38]=[C:26]3[C:25]=2[C:22]2[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][CH:23]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 22169696HCID 22169696, compound

Product 1

HCID 111641617,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF (20 mL) solution of carbonyldiimidazole (CDI), (1.7 g, 10.5 mmol) was added 1-(4,5-bis(4-chlorophenyl)pyridazin-3-yl)hydrazine (0.7 g, 2.1 mmol). The resultant brown solution was stirred at RT for 15 min. After this time, the reaction solution was poured into water (50 mL). The resultant pale colored solid was collected by filtration. Water was used to rinse the solid thoroughly to afford 7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (0.75 g, 100%). MS (M+H)=357; 1H NMR (DMSO-d6, 500 MHz): δ 12.86 (1H, s), 8.37 (1H, s), 7.42-7.48 (4H, m), 7.35 (2H, d, J=10.0 Hz), 7.27 (2H, d, J=10.0 Hz).

Workup

  1. filtrationThe resultant pale colored solid was collected by filtration
  2. washto rinse the solid thoroughly

Sources & evidence

ORD record
ord-0c81b1894a204cf58021c74f2458761c
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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