Benzyl mercaptan → 5-benzylsulfanyl-4-chloro-2-methylpyridazin-3-one

HRID 977930Notes

Reaction equation

HRID 977930 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1Cl.[CH2:11]([SH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(O)(C)C>[CH2:11]([S:18][C:7]1[CH:6]=[N:5][N:4]([CH3:9])[C:3](=[O:10])[C:2]=1[Cl:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 8471TriethylamineHCID 1204623(2H)-Pyridazinone, 4,5-dichloro-2-methyl-

Product 1

HCID 28002595-benzylsulfanyl-4-chloro-2-methylpyridazin-3-oneYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

35.8 g (200 millimoles) of 4,5-dichloro-2-methylpyridazin-3(2H)-one are suspended in 300 ml of isopropanol and the suspension is colled to -20° C. A solution of 24.8 g (200 millimoles) of benzyl mercaptan and 20.2 g (200 millimoles) of triethylamine in 200 ml of isopropanol is added dropwise at this temperature, after which stirring is continued for 1 hour at -10° C. and overnight at room temperature. The resulting precipitate is filtered off under suction, washed with isopropanol and water and dried under reduced pressure to give 31.7 g (60%) of a product of melting point 102°-104° C.

Workup

  1. customis colled to -20° C
  2. filtrationThe resulting precipitate is filtered off under suction
  3. washwashed with isopropanol and water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7c4a636d304e4c79bf850e92a525c24d
Source dataset
uspto-grants-1987_05
Patent number
US04663324

Reaction notes

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