Ici 109,081 → 6-[p-(2-methylmercaptoacetylamino)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

HRID 463654Notes

Reaction equation

HRID 463654 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][S:17][CH2:18][C:19](Cl)=[O:20]>CC(C)=O>[CH3:16][S:17][CH2:18][C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:20]

Participants

4

Reactant 2

HCID 161928Ici 109,081HCID 111262562-(Methylsulfanyl)acetyl chloride

Product 1

HCID 131933796-[p-(2-methylmercaptoacetylamino)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinoneYield 43%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.3 g (0.1 mole) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone were stirred with 14.9 g (0.12 mole) of 2-methylmercaptoacetyl chloride and 400 ml of absolute acetone for 10 hours at room temperature. The product was filtered off under suction at 10° C., washed with cold acetone and dried at 70° C. under reduced pressure. 12.5 g (43%) of 6-[p-(2-methylmercaptoacetylamino)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone were obtained. Mp.: 220°-222° C.

Workup

  1. filtrationThe product was filtered off under suction at 10° C.
  2. washwashed with cold acetone
  3. customdried at 70° C. under reduced pressure

Sources & evidence

ORD record
ord-89e324439ec44d57b7de8e10e2aec05a
Source dataset
uspto-grants-1985_10
Patent number
US04544562

Reaction notes

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