Ici 109,081 → HCID 54547772, compound

HRID 647814Notes

Reaction equation

HRID 647814 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.[Br:16][C@@H:17]1[CH2:19][C@H:18]1[C:20](Cl)=[O:21]>O1CCCC1>[Br:16][C@@H:17]1[CH2:19][C@H: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

4

Reactant 2

HCID 161928Ici 109,081HCID 54480682HCID 54480682, compound

Product 1

HCID 54547772HCID 54547772, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4.0 g (19.7 millimoles) of 6-(p-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone are dissolved in 100 ml of absolute tetrahydrofuran by heating to 60° C., whilst stirring. The solution is allowed to cool to room temperature, 4.0 g (21.8 millimoles) of trans-2-bromocyclopropanecarboxylic acid chloride are added dropwise and the mixture is stirred for 20 hours at room temperature and then for 1 hour under reflux. Thereafter it is concentrated to about 50 ml, water is added and the product is filtered off. It is washed with water and recrystallized from dimethylformamide/water, giving 6.5 g (94% of theory) of trans-6-[p-(2-bromocyclopropylcarbonylamino)-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone as colorless crystals of melting point 238°-239° C. (with decomposition).

Workup

  1. temperatureto cool to room temperature
  2. stirringthe mixture is stirred for 20 hours at room temperature
  3. temperaturefor 1 hour under reflux
  4. concentrationThereafter it is concentrated to about 50 ml, water
  5. additionis added
  6. filtrationthe product is filtered off
  7. washIt is washed with water
  8. customrecrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-34ba988246214cd1b44fddef626f1e5d
Source dataset
uspto-grants-1983_10
Patent number
US04410529

Reaction notes

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