Ethanol → 9-(2-hydroxyethyl)-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one
Reaction equation
O=[C:2]1[CH:8]([CH2:9][C:10]([OH:12])=O)[CH2:7][CH2:6][S:5][C:4]2[S:13][CH:14]=[CH:15][C:3]1=2.OCC[NH:19][NH2:20].[CH2:21]([OH:23])[CH3:22]>>[OH:23][CH2:21][CH2:22][C:14]1[S:13][C:4]2[S:5][CH2:6][CH2:7][CH:8]3[CH2:9][C:10](=[O:12])[NH:20][N:19]=[C:2]3[C:3]=2[CH:15]=1Participants
4
Procedure
A mixture of 1.4 g of 4-oxo-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid and 1.5 g of 2-hydroxyethylhydrazine in 50 ml of ethanol is refluxed under heating for 10 hours. After the mixture is concentrated, to the residue is added water and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate and concentrated. To the residue is added isopropyl ether and the solution is allowed to stand. The precipitated crystals are collected by filtration and recrystallized from isopropyl alcohol to give 1.7 g of 9-(2-hydroxyethyl)-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one as pale yellow crystals, melting at 165°-167° C.
Workup
- temperatureis refluxed
- temperatureunder heating for 10 hours
- concentrationAfter the mixture is concentrated, to the residue
- additionis added water
- extractionthe mixture is extracted with ethyl acetate
- washThe extract is washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- additionTo the residue is added isopropyl ether
- filtrationThe precipitated crystals are collected by filtration
- customrecrystallized from isopropyl alcohol
Sources & evidence
- ORD record
- ord-d61746fa17174740ae4ce7a061ec615f
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05329016
Reaction notes
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