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

HRID 2224255ノート

反応式

HRID 2224255 の反応式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[C:15]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:16]([NH:20][NH2:21])[N:17]=[N:18][CH:19]=1.O>C1COCC1>[Cl:13][C:14]1[CH:19]=[N:18][N:17]2[C:1](=[O:2])[NH:21][N:20]=[C:16]2[C:15]=1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 597168331-(5-Chloro-4-(4-chlorophenyl)pyridazin-3-yl)hydrazine

生成物 1

HCID 597168567-chloro-8-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 1,1′-carbonyldiimidazole (1.78 g, 11 mmol) in THF (10 mL) at RT was added a suspension of 1-(5-chloro-4-(4-chlorophenyl)pyridazin-3-yl)hydrazine (560 mg, 2.19 mmol) in THF (10 mL). After addition, the reaction became a clear solution and was stirred at RT for 1 h. The reaction mixture was then poured into water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturated NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. To the obtained residue was added EtOAc (20 mL), and the resulting yellow precipitate was collected by filtration and washed with hexane to give the title compound, 7-chloro-8-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one as a yellow solid (300 mg, 61%). LC/MS (method A): RT=2.86 min, (M+H)+=281.

後処理

  1. additionAfter addition
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with saturated NaCl
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionTo the obtained residue was added EtOAc (20 mL)
  8. filtrationthe resulting yellow precipitate was collected by filtration
  9. washwashed with hexane

出典と根拠

ORDレコード
ord-fa59e7618c314415a3633963e532abc6
出典データセット
uspto-grants-2008_05
特許番号
US07378418B2

反応ノート

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