Chloroacetyl chloride → 6-(p-Chloroacetylaminophenyl)-4,5-dihydropyridaz-3-one

HRID 354674

Reaction equation

HRID 354674 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18]>C1C=CC=CC=1>[Cl:15][CH2:16][C:17]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:18]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 6771076-(p-Chloroacetylaminophenyl)-4,5-dihydropyridaz-3-oneYield 81.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30.2 g (0.16 mole) of 6-(p-aminophenyl)-4,5-dihydropyridaz-3-one, 18.1 g (0.16 mole) of chloroacetyl chloride and 150 ml of absolute benzene are refluxed for 2 hours. The product is filtered off at room temperature, washed first with benzene and then with water, and dried under reduced pressure at 80° C. 34.6 g (81% of theory) of 6-(p-chloroacetylaminophenyl)-4,5-dihydropyridaz-3-one are obtained as a beige solid which, after recrystallization from dimethylformamide/water, melts, with decomposition, at 233° C.

Workup

  1. filtrationThe product is filtered off at room temperature
  2. washwashed first with benzene
  3. dry with materialwith water, and dried under reduced pressure at 80° C

Sources & evidence

ORD record
ord-13c388ee19f04ac3b777292122a83c54
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Linked notes

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