6-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one → 6-[p-(2,2-dichlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 647811Notes

Reaction equation

HRID 647811 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][C:16]1([Cl:22])[CH2:18][CH:17]1[C:19](Cl)=[O:20]>O1CCCC1>[Cl:15][C:16]1([Cl:22])[CH2:18][CH:17]1[C:19]([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:20]

Participants

4

Reactant 2

HCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 129358302,2-Dichlorocyclopropanecarbonyl chloride

Product 1

HCID 128073376-[p-(2,2-dichlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (31.7 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-3(2H)-pyridazinone and 6.6 g (38.1 millimoles) of 2,2-dichlorocyclopropanecarboxylic acid chloride in 100 ml of absolute tetrahydrofuran are refluxed for 6 hours. The product is filtered off at 10° C., washed first with tetrahydrofuran and then with water, and recrystallized from dimethylformamide/water. 7.5 g (73% of theory) of 6-[p-(2,2-dichlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone are obtained as colorless crystals, of melting point 267°-268° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed first with tetrahydrofuran
  3. customwith water, and recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-da724ac71d984ac4b5ffc9678921eb11
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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