Water → 6-[5-(1-Imidazolylmethyl)-thien-2-yl]-3-oxo-2-phenyl-2,3,4,5-tetrahydro-pyridazine

HRID 236276Notes

Reaction equation

HRID 236276 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[S:11][C:10]([C:12](=O)[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:9][CH:8]=1.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>C(O)C>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[CH2:6][C:7]1[S:11][C:10]([C:12]2[CH2:13][CH2:14][C:15](=[O:17])[N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:26]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7516PhenylhydrazineHCID 704292984-[5-(1-Imidazolylmethyl)-thien-2-yl]-4-oxobutyric acid

Product 1

HCID 540232496-[5-(1-Imidazolylmethyl)-thien-2-yl]-3-oxo-2-phenyl-2,3,4,5-tetrahydro-pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.64 g of 4-[5-(1-imidazolylmethyl)-thien-2-yl]-4-oxobutyric acid, 1.12 g phenylhydrazine, 40 ml water and 40 ml ethanol was stirred for 10 hours under reflux. After cooling the mixture was evaporated, the residue shaken with chloroform/dilute caustic soda solution, the chloroform phase washed with water, dried and evaporated. The residue was recrystallized from diisopropyl ether/ethyl acetate.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling the mixture
  3. customwas evaporated
  4. stirringthe residue shaken with chloroform/dilute caustic soda solution
  5. washthe chloroform phase washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was recrystallized from diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-0d5b4165a0e54019863f2931f4ff7dd4
Source dataset
uspto-grants-1987_02
Patent number
US04643998

Reaction notes

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