Benzyl Chloride → 5-(benzylthio)-4-chloro-2-phenylpyridazin-3(2H)-one

HRID 977928Notes

Reaction equation

HRID 977928 reaction equation
ClC1C(=O)N(C2C=CC=CC=2)N=CC=1Cl.[Cl:16][C:17]1[C:18](=[O:30])[N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]=[CH:21][C:22]=1[SH:23].S.[Na].[CH2:33](Cl)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[OH-].[Na+].[OH-].[NH4+]>>[CH2:33]([S:23][C:22]1[CH:21]=[N:20][N:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18](=[O:30])[C:17]=1[Cl:16])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 6

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 728134,5-Dichloro-2-phenyl-3(2H)-pyridazinone2×HCID 20204599HCID 20204599, compound2×HCID 86586439Sodium hydrogen sulphide

Product 1

HCID 7358005-(benzylthio)-4-chloro-2-phenylpyridazin-3(2H)-one

Procedure

Compounds of the type IV are known, but the conventional methods of preparation entail two stages, starting from the dihalo compound II, or give undesirable by-products. Chem. Abstr. 68, (1968), 2906 c describes the preparation of 4-chloro-5-mercapto-2-phenylpyridazin-3(2H)-one (V) starting from 4,5-dichloro-2-phenylpyridazin-3(2H)-one (II, R1 =C6H5, X=Cl) and sodium hydrogen sulfide, the product (V) being reacted with benzyl chloride and sodium hydroxide and ammonium hydroxide to give the desired compound 5-benzylthio-4-chloro-2-phenyl-pyridazin-3-(2H)-one. ##STR5##

Workup

  1. customthe conventional methods of preparation entail two stages
  2. customgive undesirable by-products

Sources & evidence

ORD record
ord-103b01ae19844906b7c5376268d9426c
Source dataset
uspto-grants-1987_05
Patent number
US04663324

Reaction notes

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