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

HRID 236275Notes

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.[CH3:19][NH:20][NH2:21]>O>[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:20]([CH3:19])[N:21]=2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 8.7 g of 4-[5-(1-imidazolylmethyl)-thien-2-yl]-4-oxobutyric acid, 2.9 ml methylhydrazine and 100 ml water was heated at 90° C. for 2 hours. After cooling, the precipitated solid was filtered off, dissolved in chloroform, the chloroform phase washed with dilute caustic soda solution and with water, dried over sodium sulfate and evaporated. The residue was purified by column chromatography (Silica gel//chloroform) and finally recrystallized from ethanol.

Workup

temperatureAfter cooling
filtrationthe precipitated solid was filtered off
dissolutiondissolved in chloroform
washthe chloroform phase washed with dilute caustic soda solution and with water
dry with materialdried over sodium sulfate
customevaporated
customThe residue was purified by column chromatography (Silica gel//chloroform)
customfinally recrystallized from ethanol

Sources & evidence

ORD record: ord-facaa37b75c84a20a64edf600cdada5b
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04643998

Reaction notes

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