Water → HCID 13084137, compound

HRID 67262Notes

Reaction equation

S(Cl)(Cl)=O.Cl[C:6]1C=CC(N2C(C)=C(CCC)C(=O)C(C(O)=O)=N2)=CC=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:38]([CH2:39][CH2:40][CH2:41][CH3:42])=[CH:37][C:36](=[O:43])[C:35]([C:44]([OH:46])=[O:45])=[N:34]2)=[CH:29][CH:28]=1.O>CO>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:38]([CH2:39][CH2:40][CH2:41][CH3:42])=[CH:37][C:36](=[O:43])[C:35]([C:44]([O:46][CH3:6])=[O:45])=[N:34]2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 25 ml of methanol, cooled to -5° C., there is added 2.38 g (0.02 mol) of thionyl chloride. To the ice cooled solution is added 2.85 g (0.0093 mol) of the mixture of 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-5-n-propyl-6-methyl pyridazine-3-carboxylic Acid and 1-(4-chlorophenyl)-1,4-dihydro-4-oxo-6-n-butyl pyridazine-3-carboxylic Acid dissolved in 25 ml of methanol. The solution is stirred at 0° C. for 1/2 hr. and at room temperature for 18 hrs. To the solution is added 250 ml of water and the oil suspension formed is stirred at room temperature for 1 hr. The suspension is extracted with 3 (100 ml) portions of methylene dichloride and the extract is dried over magnesium sulfate and concentrated in vacuo to afford 2.9 g of mixed products (oil). The mixture is separated using a silica gel dry column and ethyl acetate as eluent to afford 0.5 g (17% yield of example 30 (oil) and 0.5 g (17% yield) of example 29 (semi-solid).

Workup

waitand at room temperature for 18 hrs
customthe oil suspension formed
stirringis stirred at room temperature for 1 hr
extractionThe suspension is extracted with 3 (100 ml) portions of methylene dichloride
dry with materialthe extract is dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fecb7a00eb934c129681cc7edb4f464b
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04345934

Reaction notes

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