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

HRID 647812Notes

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.[Cl:16][C:17]1([Cl:23])[CH2:19][CH:18]1[C:20](Cl)=[O:21]>O1CCCC1>[Cl:16][C:17]1([Cl:23])[CH2:19][CH:18]1[C:20]([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:21]

Participants

Conditions

Temperature: 60 °C

Procedure

5.0 g (24.6 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are dissolved in 100 ml of absolute tetrahydrofuran by stirring and heating to 60° C. The solution is allowed to cool to room temperature, 5.15 g (29.7 millimoles) of 2,2-dichlorocyclopropanecarboxylic acid chloride, dissolved in 10 ml of absolute tetrahydrofuran, are added dropwise and the mixture is then stirred for 6 hours under reflux. Thereafter it is concentrated to about 50 ml and the product is filtered off at 10° C., washed with water and recrystallized from dimethylformamide/water. 5.0 g (60% of theory) of 6-[p-(2,2-dichlorocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone are obtained as colorless crystals, of melting point 252°-253° C.

Workup

temperatureto cool to room temperature
additionare added dropwise
stirringthe mixture is then stirred for 6 hours
temperatureunder reflux
concentrationThereafter it is concentrated to about 50 ml
filtrationthe product is filtered off at 10° C.
washwashed with water
customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record: ord-96220c68afc94d9e9fb658ff904ae3fd
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410529

Reaction notes

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