Acetone → 6-[(4-Chlorophenyl)thio]-2,3-dihydro-2-(phenyl)5-methyl-3-oxo-4-pyridazinecarbonitrile

HRID 1720250Notes

Reaction equation

HRID 1720250 reaction equation
CC(=O)C.CCOC(C(C1(C#N)CCCC1)C#N)=O.C([O-])(=O)C.[NH4+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[C:34]([CH3:49])=[C:35]([C:47]#[N:48])[C:36](=[O:46])[N:37]([C:39]3[CH:44]=[CH:43][C:42](Cl)=[CH:41][CH:40]=3)[N:38]=2)=[CH:28][CH:27]=1>CCO>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[C:34]([CH3:49])=[C:35]([C:47]#[N:48])[C:36](=[O:46])[N:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:38]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 517165Ammonium AcetateHCID 152939226-[(4-Chlorophenyl)thio]-2,3-dihydro-2-(4-chlorophenyl)5-methyl-3-oxo-4-pyridazinecarbonitrileHCID 16226777Ethyl 2-cyano-2-(1-cyanocyclopentyl)acetate

Product 1

HCID 224176866-[(4-Chlorophenyl)thio]-2,3-dihydro-2-(phenyl)5-methyl-3-oxo-4-pyridazinecarbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction of 1.8 g (5.9 mmol) of 1-[(4-chlorophenyl)thio]-1-[phenyl)hydmzono]-2-propanone, 1.5 ml of ethylcyano acetate and 750 mg of ammonium acetate as in Example 22, yielded1.29 g of 6-[(4-chlorophenyl)thio]- 2,3-dihydro-2-(4-chlorophenyl)5-methyl-3-oxo-4-pyridazinecarbonitrile, mp 180°-182° C. (EtOH).

Sources & evidence

ORD record
ord-be625ceaa22447e4a14da48688529b83
Source dataset
uspto-grants-1996_04
Patent number
US05506228

Reaction notes

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